| Identification | Back Directory | [Name]
6-Azaindole-3-carboxaldehyde | [CAS]
25957-65-7 | [Synonyms]
6-Azaindole-3-aldehyde
6-Azaindole-3-carbaldehyde
3-c]pyridine-3-carbaldehyde
6-Azazindole-3-carboxyaldehyde.
H-pyrrolo[2,3-c]pyridine-3-carbaldehyde
1H-Pyrrolo[2,3-c]pyridine-3-carboxaldehyde
1-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde (7CI) | [Molecular Formula]
C8H6N2O | [MDL Number]
MFCD08272238
| [MOL File]
25957-65-7.mol | [Molecular Weight]
146.15 |
| Chemical Properties | Back Directory | [Boiling point ]
383.2±22.0 °C(Predicted) | [density ]
1.368 | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
13.16±0.40(Predicted) | [Appearance]
Off-white to gray Solid | [InChI]
InChI=1S/C8H6N2O/c11-5-6-3-10-8-4-9-2-1-7(6)8/h1-5,10H | [InChIKey]
IAMJYHYPXUQXGI-UHFFFAOYSA-N | [SMILES]
C1=NC=CC2C(C=O)=CNC1=2 | [CAS DataBase Reference]
25957-65-7 |
| Hazard Information | Back Directory | [Uses]
1H-Pyrrolo[2,3-c]pyridine-3-carbaldehyde is used in preparation of α,β-unsaturated ketone derivatives as microtubule inhibitors for treatment of tumor. | [Synthesis]
GENERAL STEPS: To a solution of 6-azaindole (0.400 g; 3.386 mmol) in a solvent mixture of 1,2-dichloroethane (10 mL) and nitromethane (10 mL), cooled to 0°C. A mixture of 1,1-dichlorodimethyl ether (1.544 mL; 16.92 mmol) and aluminum trichloride (1.500 g; 11.25 mmol) was slowly added dropwise under argon protection for a controlled time of 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of water and saturated sodium bicarbonate solution. The reaction mixture was extracted with a solvent mixture of dichloromethane and ethanol (9:1 v/v, 6 x 100 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude product 1H-pyrrolo[2,3-c]pyridine-3-carboxaldehyde (0.295 g, 60% yield), which could be used in the subsequent reaction without further purification. Product characterization data: ESI/APCI(+) m/z: 147 ([M + H]+); ESI/APCI(-) m/z: 145 ([M - H]-). 1H NMR (DMSO-d6) δ: 10.01 (1H, s), 8.88 (1H, s), 8.50 (1H, s), 8.33 (1H, d), 8.00 (1H, d). d). | [References]
[1] Patent: WO2013/45516, 2013, A1. Location in patent: Page/Page column 200 |
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