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4-Bromo-6-(trifluoromethyl)-1H-indazole

4-Bromo-6-(trifluoromethyl)-1H-indazole

4-Bromo-6-(trifluoromethyl)-1H-indazole

CAS No.: 1000342-95-9

Category Products

Cat.NO.:A417797 Purity:97%

Product Details of [ 1000342-95-9 ]

CAS No. :	1000342-95-9
Formula :	C₈H₄BrF₃N₂
M.W :	265.03
SMILES Code :	FC(F)(F)C1=CC(Br)=C2C=NNC2=C1
MDL No. :	MFCD09026956
InChI Key :	JRUCLQINUHVRJW-UHFFFAOYSA-N
Pubchem ID :	24729232

Safety of [ 1000342-95-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 1000342-95-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	9
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	48.8
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	28.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.47
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.13
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.5
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.9
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.65
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.86
Solubility	0.0362 mg/ml ; 0.000137 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.4
Solubility	0.105 mg/ml ; 0.000397 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.65
Solubility	0.00592 mg/ml ; 0.0000223 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.69 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12’782’590 molecules and tested on 40 external molecules (r² = 0.94)	1.76

Application In Synthesis of [ 1000342-95-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1000342-95-9 ]

[ 1000342-95-9 ] Synthesis Path-Downstream 1~35

1
[ 110-87-2 ]
[ 1000342-95-9 ]
[ 1425932-71-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With toluene-4-sulfonic acid; In tetrahydrofuran; for 18h;Inert atmosphere; Reflux;	Referential example 25 (l-(Tetrahydro-2H-pyran-2-yl)-6-(trifluoromethyl)-lH-indazol-4-yl)methanamine (127) step 1 : A round-bottom flask was charged with 4-bromo-6-(trifluoromethyl)-lH-indazole (1.00 g, 3.8 mmol), TsOH monohydrate (27 mg, 0.15 mmol), 3,4-dihydro-2H-pyran (1.59 g, 18.9 mmol), and THF (25 mL). The reaction mixture was degassed with nitrogen and heated under reflux for 18 h, and then the solvent was removed in vacuo. The residue was purified by S1O2 chromatography to afford 4-bromo-l – (tetrahydro-2H-pyran-2-yl)-6-(trifluoromethyl)-lH-indazole (1.03 g, 78percent) as a yellow oil. MS (ESI) m/z: 265.2 [(M – THP group)+l]+.

References: [1]Patent: WO2013/26914,2013,A1 .Location in patent: Page/Page column 122.

2
[ 1000342-95-9 ]
[ 1425932-73-5 ]

References: [1]Patent: WO2013/26914,2013,A1 .

3
[ 1000342-95-9 ]
[ 1425932-72-4 ]

References: [1]Patent: WO2013/26914,2013,A1 .

4
(4-((2-hydroxyethyl)carbamoyl)phenyl)boronic acid [ No CAS ]
[ 1000342-95-9 ]
[ 76-05-1 ]
[ 1454293-91-4 ]

Yield	Reaction Conditions	Operation in experiment
30%		EXAMPLE 130: N-(2-hydroxyethyl)-4-(6-(trifiuoromethyl)-lH-indazol-4- yl)benzamide [0550] A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-lH-indazole (0.300 g, 1.132 mmol), (4-((2-hydroxyethyl)carbamoyl)phenyl)boronic acid (0.237 g, 1.132 mmol) and PdCl2(dppf) (0.041 g, 0.057 mmol) in dioxane (10 mL) and aqueous saturated NaHC03 (3 mL). The resulting yellow suspension was heated at 140°C for 60 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with 40percent> ACN (containing 0.035percent) TFA) in H20 (containing 0.05percent TFA) over a period of 4.5 minutes. The product-containing fractions were combined and volatiles removed in vacuo to give a TFA salt of the title compound as white solid (0.12 g, 30percent). 1H NMR (400 MHz, CD3OD) delta ppm 3.56 (t, J=5.81 Hz, 2 H), 3.75 (t, J=5.81 Hz, 2 H), 7.49 (d, J=1.01 Hz, 1 H), 7.78-7.89 (m, 2 H), 7.93 (s, 1 H), 8.00-8.10 (m, 2 H), 8.21-8.32 (m, 1 H); ESI-MS m/z [M+H]+ calc’d for Ci7Hi4F3N302, 350.1; found 350.1.

References: [1]Patent: WO2013/130855,2013,A1 .Location in patent: Paragraph 0549; 0550.

5
[ 1000342-95-9 ]
[ 76-05-1 ]
[ 628692-15-9 ]
4-(2-methoxypyrimidin-5-yl)-6-(trifluoromethyl)-1H-indazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		EXAMPLE 246: 4 2-methoxypyrimidin-5-yl)-6-(trifluoromethyl)-lH-indazole [0784] A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-lH-indazole (0.1 g, 0.377 mmol), (2-methoxypyrimidin-5-yl)boronic acid (0.076 g, 0.491 mmol) and PdCl2(dppf) (0.014 g, 0.019 mmol) in dioxane (8 mL) and aqueous saturated NaHC03 (2 mL). The resulting light brown suspension was heated at 140°C for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with a gradient of 35-40percent ACN (containing 0.035percent TFA) in H20 (containing 0.05percent TFA) over a period of 8 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as white solid (0.043 g, 39percent). 1H NMR (400 MHz, DMSO-<) delta ppm 4.03 (s, 3 H), 7.60 (d, J=1.01 Hz, 1 H), 8.00 (s, 1 H), 8.34-8.52 (m, 1 H), 9.06 (s, 2 H); ESI-MS m/z [M+H]+ calc’d for Ci3H9F3N40, 295.1; found 295.15.

References: [1]Patent: WO2013/130855,2013,A1 .Location in patent: Paragraph 0783; 0784.

6
[ 1015480-87-1 ]
[ 1000342-95-9 ]
[ 76-05-1 ]
4-(3,6-dimethoxypyridazin-4-yl)-6-(trifluoromethyl)-1H-indazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4%		EXAMPLE 248 : 4-(3 ,6-dimethoxypyridazin-4-yl)-6-(trifluoromethyl)- lH-indazole [0788] A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-lH-indazole (0.15 g, 0.566 mmol),(3,6-dimethoxypyridazin-4-yl)boronic acid (0.135 g, 0.736 mmol) and PdCl2(dppf) (0.021 g, 0.028 mmol) in dioxane (10 mL) and aqueous saturated NaHC03 (3 mL). The resulting light brown suspension was heated at 140°C for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with a gradient of 40-45percent ACN (containing 0.035percent TFA) in H20 (containing 0.05percent TFA) over a period of 6.5 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as a light brown solid (8 mg, 4percent). 1H NMR (400 MHz, DMSO-d6) delta ppm 3.97 (s, 3 H), 4.03 (s, 3 H), 7.42 (s, 1 H), 7.55 (d, J=1.01 Hz, 1 H), 8.05 (s, 1 H), 8.14 (s, 1 H), 13.74 (s, 1 H); ESI-MS m/z [M+H]+ calc’d for Ci4HiiF3N402, 325.1; found 325.16.

References: [1]Patent: WO2013/130855,2013,A1 .Location in patent: Paragraph 0787; 0788.

7
[ 1000342-95-9 ]
[ 76-05-1 ]
[ 459856-12-3 ]
4-(6-methoxy-2-methylpyridin-3-yl)-6-(trifluoromethyl)-1H-indazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		EXAMPLE 249: 4-(6-methoxy-2-methylpyridin-3-yl)-6-(trifluoromethyl)-lH- indazole [0790] A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-lH-indazole (0.15 g, 0.566 mmol), (6-methoxy-2-methylpyridin-3-yl)boronic acid (0.123 g, 0.736 mmol) and PdCl2(dppf) (0.021 g, 0.028 mmol) in dioxane (10 mL) and aqueous saturated NaHC03 (3 mL). The resulting light brown suspension was heated at 140°C for 45 minutes in microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with 45percent ACN (containing 0.035percent) TFA) in H20 (containing 0.05percent TFA) over a period of 6.5 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as a light brown oil (82 mg, 47percent). 1H NMR (400 MHz, OMSO-de) delta ppm 2.30 (s, 3 H), 3.93 (s, 3 H), 6.75-6.86 (m, 1 H), 7.29 (d, J=1.26 Hz, 1 H), 7.72 (d, J=8.34 Hz, 1 H), 7.90-8.03 (m, 2 H); ESI-MS m/z [M+H]+ calc’d for Ci5Hi2F3N30, 308.1; found 308.15.

References: [1]Patent: WO2013/130855,2013,A1 .Location in patent: Paragraph 0789; 0790.

8
[ 864754-16-5 ]
[ 1000342-95-9 ]
[ 76-05-1 ]
ethyl2-(4-(6-(trifluoromethyl)-1H-indazol-4-yl)-1H-pyrazol-1-yl)acetate trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%		EXAMPLE 260: ethyl 2-(4-(6-(trifluoromethyl)-lH-indazol-4-yl)-lH-pyrazol-l- yl)acetate [0812] A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-lH-indazole (0.3 g, 1.132 mmol), ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazol-l- yl)acetate (0.349 g, 1.245 mmol) and PdCl2(dppf) (0.041 g, 0.057 mmol) in dioxane (10 mL) and aqueous saturated NaHC03 (3 mL). The resulting light brown suspension was heated at 140°C for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with a gradient of 40-45percent ACN (containing 0.035percent TFA) in H20 (containing 0.05percent TFA) over a period of 6.5 minutes. The product-containing fractions were combined and the volatiles were removed via rotary evaporation to give a TFA salt of the title compound as a light brown solid (0.14 g, 37percent). 1H NMR (400 MHz, OMSO-d6) delta ppm 1.24 (t, J=7.07 Hz, 3 H), 4.19 (q, J=7.16 Hz, 2 H), 5.15 (s, 2 H), 7.60 (d, J=1.01 Hz, 1 H), 7.77 (s, 1 H), 8.27 (d, J=0.76 Hz, 1 H), 8.53 (s, 1 H), 8.63 (s, 1 H), 13.64 (s, 1 H); ESI-MS m/z [M+H]+ calc’d for Ci5Hi3F3N402, 339.1; found 339.

References: [1]Patent: WO2013/130855,2013,A1 .Location in patent: Paragraph 0811; 0812.

9
[ 1072945-86-8 ]
[ 1000342-95-9 ]
[ 76-05-1 ]
methyl 5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinatetrifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 269: methyl 5-(6-(trifluoromethyl)-lH-indazol-4-yl)picolinate [0830] A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-lH-indazole (0.732 g, 2.76 mmol), (6-(methoxycarbonyl)pyridin-3-yl)boronic acid (0.5 g, 2.76 mmol) and PdCl2(dppf) (0.101 g, 0.138 mmol) in dioxane (10 mL) and aqueous saturated NaHC03 (3 mL). The resulting light brown suspension was heated at 140°C for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated. The residue was diluted with DCM, washed with water, and the volatiles removed via rotary evaporation. The crude product was purified by CombiFlash® chromatography (0-30percent MeOH in DCM over 180 minutes). The product-containing fractions were combined and concentrated by rotary evaporation to give product with some impurities (0.28 g). A portion of the product (20 mg) was re-purified by preparative HPLC, eluting with 40percent ACN (containing 0.035percent TFA) i Details Products CAS 57-22-7 Read more Products CAS 57-52-3 Read more Products CAS 53-57-6 Read more Reviews There are no reviews yet. Be the first to review “4-Bromo-6-(trifluoromethyl)-1H-indazole” Cancel reply Your email address will not be published. Required fields are marked * Your rating * Your review * Name * Email * Save my name, email, and website in this browser for the next time I comment. Previous 4-Bromo-7-chloro-1H-pyrrolo[3,2-c]pyridine Next 5-Bromo-6-iodo-1H-indole Easy CDMO Easy CDMO is China TOP100 CDMO company. We believe: Easy CDMO, Medicinal Chemical is Big. More than 100 scientists are serving you. Quick Links About Us Products Blog Contacts Support Links Privacy Policy Term And Condition Locations Office address: Chenxun Technology Building, No. 633, Jinzhong Road, Changning District, Shanghai info@easycdmo.com +8602161734564 © Copyright Easy CDMO 2025. All Rights Reserved.