| Identification | Back Directory | [Name]
7-AZAINDOLE-3-CARBOXALDEHYDE | [CAS]
4649-09-6 | [Synonyms]
3-ForMyl-7-azaindole
7-azaindole-3-carbaldehyde
3-b]pyridine-3-carbaldehyde
7-AZAINDOLE-3-CARBOXALDEHYDE
7-Azazindole-3-carboxyaldehyde.
3-FORMYL-PYRROLO[2,3-B]PYRIDINE
7-Azaindole-3-carboxaldehyde 97%
3-FORMYL-1H-PYRROLO[2,3-B]PYRIDINE
7-Azaindole-3-carboxaldehyde, >=97%
Pyrrolo[2,3-b]pyridine-3-carboxaldehyde
1H-pyrrolo[5,4-b]pyridine-3-carbaldehyde
1H-PYRROLO[2,3-B]PYRIDINE-3-CARBALDEHYDE
1H-PYRROLO[2,3-B]PYRIDINE-3-CARBOXALDEHYDE
1H-pyrrolo[5,4-b]pyridine-3-carboxaldehyde
2,9-diazabicyclo[4.3.0]nona-2,4,7,10-tetraene-7-carbaldehyde
1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 3-Formyl-1H-pyrrolo[2,3-b]pyridine | [Molecular Formula]
C8H6N2O | [MDL Number]
MFCD03407363 | [MOL File]
4649-09-6.mol | [Molecular Weight]
146.15 |
| Chemical Properties | Back Directory | [Melting point ]
216-220 °C | [Boiling point ]
379.6±42.0 °C(Predicted) | [density ]
1.31 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
solid | [pka]
6.07±0.20(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C8H6N2O/c11-5-6-4-10-8-7(6)2-1-3-9-8/h1-5H,(H,9,10) | [InChIKey]
KAIWRKYDYWYFIT-UHFFFAOYSA-N | [SMILES]
C12NC=C(C=O)C1=CC=CN=2 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow solid | [Uses]
Reactant for preparation of:
- Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
- Inhibitors of BACE-1 activity
- Prostate cancer invasion and migration inhibitors
- CDK2 kinase inhibitors
- Cell division cycle 7 kinase inhibitors
- Inhibitor of oncogenic B-Raf kinase with potent antimelanoma activity
- Antidiabetic agents
- Inhibitors of brassinin glucosyltransferase
| [Uses]
7-Azaindole-3-Carboxaldehyde is a reagent used in the preparation of biologically active Azaindoles.
| [Synthesis]
1H-pyrrolo[2,3-b]pyridine (11.80 g, 100 mmol) was suspended in 33% aqueous acetic acid (200 mL) at room temperature, followed by the addition of hexamethylenetetramine (16.8 g, 120 mmol). The reaction mixture was heated to 110-120 °C (oil bath temperature) and stirred continuously at this temperature for 15 hours. Upon completion of the reaction, the mixture was cooled to room temperature, at which point a large amount of solid precipitated. The suspension was poured into a 2 L beaker containing ice and the reaction flask was rinsed with 50 mL of water. Subsequently, saturated sodium bicarbonate solution was slowly added for neutralization. After completion of neutralization, the solid product was collected by filtration and washed with distilled water. The product was dried in air to give 1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (9.5 g, 65% yield) as a white solid.EI-HRMS analysis results: m/e calculated value C8H6N2O (M+) 146.0480, measured value 146.0478. | [References]
[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7577 - 7589
[2] Patent: US2006/84674, 2006, A1. Location in patent: Page/Page column 7
[3] Patent: US2004/224973, 2004, A1. Location in patent: Page 32
[4] Chinese Chemical Letters, 2010, vol. 21, # 3, p. 297 - 300
[5] Patent: US2012/245178, 2012, A1. Location in patent: Page/Page column 12 |
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