| Identification | Back Directory | [Name]
(1H-PYRROLO[2,3-B]PYRIDIN-5-YL)-METHANOL | [CAS]
849067-97-6 | [Synonyms]
5-HYDROXYMETHYL-7-AZAINDOLE
1H-Pyrrolo[2,3-b]pyridine-5-methanol
(1H-PYRROLO[2,3-B]PYRIDIN-5-YL)-METHANOL
5-(hydroxyMethyl)-1h-pyrrolo[2,3-b]pyridine | [Molecular Formula]
C8H8N2O | [MDL Number]
MFCD08457786 | [MOL File]
849067-97-6.mol | [Molecular Weight]
148.16 |
| Chemical Properties | Back Directory | [Melting point ]
126-127°C | [density ]
1.360±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [form ]
solid | [pka]
13.84±0.10(Predicted) | [Appearance]
White to off-white Solid | [InChI]
1S/C8H8N2O/c11-5-6-3-7-1-2-9-8(7)10-4-6/h1-4,11H,5H2,(H,9,10) | [InChIKey]
HECHZAPQJASYJL-UHFFFAOYSA-N | [SMILES]
OCc1cnc2[nH]ccc2c1 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
2933998090 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Uses]
(1H-Pyrrolo[2,3-b]pyridin-5-yl)methanol is used as a pharmaceutical intermediate.
| [Synthesis]
General procedure for the synthesis of (1H-pyrrolo[2,3-b]pyridin-5-yl)methanol from methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate:
Step C: Preparation of (1H-pyrrolo[2,3-b]pyridin-5-yl)methanol
[0249] Methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate (75 mg, 0.394 mmol) was dissolved in THF at 0 °C and lithium aluminum hydride (45 mg, 1.18 mmol) was added slowly. The reaction mixture was gradually warmed to room temperature followed by refluxing for 12 hours. After completion of the reaction, it was cooled to room temperature and quenched with water. The reaction mixture was extracted with ethyl acetate, the organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated to give (1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (57 mg, 98% yield).
Product characterization data:
1H NMR (500 MHz, DMSO-d6) δ: 11.50 (1H, bs), 8.166-8.163 (1H, d), 7.862-7.860 (1H, d), 7.43-7.42 (1H, d), 6.41-6.40 (1H, d), 5.10-5.08 (1H, t), 4.58-4.57 ( 2H, d).
FIA MS, m/z [MH]+ 149.1. | [References]
[1] Patent: WO2005/28475, 2005, A2. Location in patent: Page/Page column 142-143; 222 |
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