Cat.NO.:A509828 Purity:98%
Product Details of Pyrrole-2-carboxaldehyde
| CAS No. : | 1003-29-8 |
| Formula : |
C5H5NO |
| M.W : |
95.10
|
| SMILES Code : | O=CC1=CC=CN1 |
| MDL No. : | MFCD00005217 |
| InChI Key : | ZSKGQVFRTSEPJT-UHFFFAOYSA-N |
| Pubchem ID : | 13854 |
Safety of Pyrrole-2-carboxaldehyde
| GHS Pictogram: |  |
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
Application In Synthesis of Pyrrole-2-carboxaldehyde
* 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 [ 1003-29-8 ]
[ 1003-29-8 ] Synthesis Path-Downstream 1~16
- 1
[ 1003-29-8 ]
[ 58656-98-7 ]
- 4-(2-Formyl-pyrrol-1-yl)-benzoic acid tert-butyl ester [ No CAS ]
- 2
- [ 1003-29-8 ]
[ 7089-68-1 ]
[ 1779-49-3 ]
[ 207505-40-6 ]
References: [1]Tetrahedron Letters,1998,vol. 39,p. 2617 – 2620.
- 3
- [ 1003-29-8 ]
[ 766-36-9 ]- (Z)-5-((1H-pyrrol-2-yl)methylene)-3-ethyl-4-methyl-1H-pyrrol-2(5H)-one [ No CAS ]
- 4
- [ 1003-29-8 ]
[ 326-62-5 ]- (Z)-2-(2-fluorophenyl)-3-(1H-pyrrol-2-yl)acrylonitrile [ No CAS ]
- 5
- [ 1003-29-8 ]
[ 656-35-9 ]- 2-(2,4-difluoro-phenyl)-3-(1<i>H</i>-pyrrol-2-yl)-acrylonitrile [ No CAS ]
- 6
- [ 1003-29-8 ]
[ 75279-55-9 ]- 2-(2-chloro-6-fluoro-phenyl)-3-(1<i>H</i>-pyrrol-2-yl)-acrylonitrile [ No CAS ]
- 7
[ 931-34-0 ]- [ 1003-29-8 ]
- 8
- [ 1003-29-8 ]
[ 99365-48-7 ]- [ 276251-73-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 96% | With piperidine; In isopropyl alcohol; at 85℃; for 2h; | A mixture of <strong>[99365-48-7]4-bromo-1,3-dihydro-2H-indol-2-one</strong> (0.2 g, 0.94 mmol) (see T. Kosuge et. al., Chem. Pharm. Bull. 33(4):1414-1418 (1985)), and excess pyrrole-2-carboxaldehyde (0.11 g, 1.13 mmol) (Aldrich) in 1% piperidine in 2-propanol (2 mL) was heated at 85 C for 2 h. Hot water (2 mL) was added. On cooling, the crystallized product was filtered off, washed with aqueous 2-propanol and dried. (Yield 0.26 g, 96%) |
- 9
- [ 1003-29-8 ]
[ 20348-09-8 ]- [ 312973-06-1 ]
- [ 312973-72-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 2%; 15% | Sodium methoxide (0.65 g, 0.012 mol) was added in one portion to a mixture of 2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (1.50 g, 0.01 mol) and pyrrole-2-carboxaldehyde (1.58 g, 0.016 mol) in dry DMF (10 ml). The reaction mixture was refluxed for 48 h, then cooled to room temperature, poured into crushed ice and left overnight at 4 C. The precipitated solid was filtered off, washed with water and dried. The dark solid was boiled with ethanol (150 ml) and filtered hot to remove impurities. The filtrate was evaporated to dryness under reduced pressure, and the residue was purified by silica gel chromatographed using (95:5) toluene:ethyl acetate as the mobile phase. |
- 10
- [ 1003-29-8 ]
[ 942067-98-3 ]- [ 258827-90-6 ]
- 11
- [ 1003-29-8 ]
[ 69917-80-2 ]
References: [1]Tetrahedron,2013,vol. 69,p. 8527 – 8533.
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3013 – 3024.
[3]Journal of the American Chemical Society,2017,vol. 139,p. 15801 – 15811.
[4]Chemistry – A European Journal,2018,vol. 24,p. 4957 – 4966.
[5]Patent: WO2018/53353,2018,A1 .
[6]ACS Chemical Neuroscience,2019,vol. 10,p. 1445 – 1451.
[7]Patent: US2020/72711,2020,A1 .
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3013 – 3024.
[3]Journal of the American Chemical Society,2017,vol. 139,p. 15801 – 15811.
[4]Chemistry – A European Journal,2018,vol. 24,p. 4957 – 4966.
[5]Patent: WO2018/53353,2018,A1 .
[6]ACS Chemical Neuroscience,2019,vol. 10,p. 1445 – 1451.
[7]Patent: US2020/72711,2020,A1 .
- 12
- [ 1003-29-8 ]
[ 1668-54-8 ]- [ 1465740-09-3 ]
- 13
- [ 1003-29-8 ]
[ 1120-95-2 ]- [ 1600527-79-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 34% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 20h; | General procedure: A flask was charged with 2-formylpyrrole 1 (5.00 g, 52.6 mmol), K2CO3 (8.72 g, 63.1 mmol), 2-fluoropyridine 2 (9.0 mL, 105.2 mmol) and DMF (26 mL).The mixture was heated at 100 °C for 20 h and then cooled to rt. The reaction mixturewas diluted with water, extracted with MTBE, and the organic phase was dried (MgSO4), filtered, and concentrated. The crude product was purified by chromatography on SiO2(hexanes/EtOAc, 95:5 to 85:15 v/v) to give the product 3 (5.71 g, 63percent) as a tan solid. |
References: [1]Tetrahedron Letters,2014,vol. 55,p. 2492 – 2494.
- 14
- [ 1003-29-8 ]
[ 14704-31-5 ]- 1-([1,1′-biphenyl]-3-ylmethyl)-1H-pyrrole-2-carbaldehyde [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 98% | With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; water; at 0 – 20℃; | To a stirred mixture of 1H-pyrrole-2-carbaldehyde 39 (200 mg, 2.10 mmol), TBAB (68 mg, 0.21 mmol) and <strong>[14704-31-5]3-(bromomethyl)-1,1′-biphenyl</strong> 38 (624 mg, 2.52 mmol ) in DCM was added aqueous NaOH solution (1.2 mL, 1.25 M in H2O) dropwise over a period of 30 min at 0 C. Then the mixture was allowed to warm to room temperature. After stirring overnight, the mixture was diluted with water, and extracted with DCM (3 x 30 mL). The combined organic phases were washed with 2 M HCl, saturated NaHCO3 and brine, dried with Na2SO4, filtered, concentrated and purified by silica gel chromatography to afford 43 (540 mg, 98%) as a white solid. |
- 15
- [ 1003-29-8 ]
[ 78364-55-3 ]- 6-fluoro-2-[2-((1H-pyrrol-2-yl)methylene)hydrazino]benzothiazole [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 79% | With acetic acid; In ethanol; at 80℃; for 0.166667h;Microwave irradiation; | General procedure: 2-(2-Arylidenehydrazino)-6-fluorobenzothiazoles 6a-r. General Procedure D. A mixture of compound 2 (0.0549 g, 0.0003 mol), the appropriate aromatic aldehyde (0.00033 mol) and glacial acetic acid (0.1 mL) in ethanol (5 mL) was heated under microwave (20 W) at 80 °C for 10 min. On cooling, the precipitated solid was collected by filtration, washed with water, dried and crystallized from the appropriate solvent to give the desired compounds 6a-r. |
- 16
- [ 1003-29-8 ]
[ 53137-27-2 ]
[ 931-53-3 ]- [ 106-49-0 ]
- N-(2-(cyclohexylamino)-2-oxo-1-(1H-pyrrol-2-yl)ethyl)-2,4-dimethyl-N-(p-tolyl)thiazole-5-carboxamide [ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 35% | General procedure: The aldehyde (0.8 equivalent) and amine (0.7 equivalent) were dissolved in methanol (2.0 mL) and stirred for two to 3 h depending upon the starting material. The acid (100 mg, 1 equivalent) and isocyanide (0.7 equivalent) were added in the reaction mixture and further stirred. The reaction mixture was monitored using TLC analysis.Water (4 mL) was added upon completion of the reaction.The resulted solid was filtered off and dissolved in ethyl acetate(10 mL), washed with water (2 3 mL) and dried over sodium sulphate. The crude product was purified using silica gel column chromatography. The ethyl acetate:hexane (6:4) solvent system was used for the purification of these compounds. |
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