1H-Pyrrolo[2,3-c]pyridine-3-carbaldehyde → HCID 57893484, compound

HRID 1821883Notes

Reaction equation

[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[O:11])=[CH:2]1.[C:12]1([Mg]Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[C:12]1([CH:10]([C:3]2[C:4]3[C:5](=[CH:6][N:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)[OH:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A mixture of 1H-pyrrolo[2,3-c]pyridine-3-carboxaldehyde (100 mg, 0.68 mmol) and THF (6.8 mL) was cooled to −40° C. and phenylmagnesium chloride (0.68 mL, 1.36 mmol) was added. The reaction mixture was warmed to room temperature and refluxed for 1 h. The reaction mixture was cooled to room temperature and quenched with saturated NH4Cl and then water was added. The aqueous layer was extracted with EtOAc (1×), dried (MgSO4) and filtered, and the solvent was removed. The crude material was purified by Biotage chromatography (90:10 to 85:15 methylene chloride/methanol) to give phenyl(1H-pyrrolo[2,3-c]pyridin-3-yl)methanol as a yellow solid (65.5 mg, 43%): Rf 0.11 (90:10 methylene chloride/methanol); 1H NMR (300 MHz, CD3OD) (6.09 (1H, s), 7.25-7.27 (1H, m), 7.32-7.35 (3H, m), 7.46-7.48 (3H, m), 7.96-7.97 (1H, d, J=5.6 Hz), 8.64 (1H, s); ESI MS m/z 225 [C14H12N2O+H]+; Estimated Purity: >90% by 1H NMR analysis.

Workup

temperatureThe reaction mixture was warmed to room temperature
temperaturerefluxed for 1 h
temperatureThe reaction mixture was cooled to room temperature
customquenched with saturated NH4Cl
additionwater was added
extractionThe aqueous layer was extracted with EtOAc (1×)
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent was removed
customThe crude material was purified by Biotage chromatography (90:10 to 85:15 methylene chloride/methanol)

Sources & evidence

ORD record: ord-a676ddfe8d714796a37ffd41651350dc
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608627B2

Reaction notes

Loading…