2-(1-Azidoethyl)-1-phenyl-1H-imidazo[4,5-c]pyridine → 1-(1-Phenyl-1H-imidazo[4,5-c]pyridin-2-yl)ethylamine

HRID 243043Notes

Reaction equation

[N:1]([CH:4]([C:6]1[N:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]=1)[CH3:5])=[N+]=[N-]>[Pd].CCOC(C)=O>[C:15]1([N:7]2[C:8]3[CH:13]=[CH:12][N:11]=[CH:10][C:9]=3[N:14]=[C:6]2[CH:4]([NH2:1])[CH3:5])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 2-(1-azidoethyl)-1-phenyl-1H-imidazo[4,5-c]pyridine (0.40 g, 1.50 mmol) and 10% palladium on carbon (0.10 g) in EtOAc (20 mL) was stirred under an atmosphere of hydrogen at atmospheric pressure and 20° C. for 16 h. The catalyst was removed by filtration, the filtrate concentrated in vacuo, and the resulting residue purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM) to give the title compound as a white solid (0.194 g, 54%). LCMS (method J): Rt 0.26 min, [M+H]+ 239.

Workup

customThe catalyst was removed by filtration
concentrationthe filtrate concentrated in vacuo
customthe resulting residue purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM)

Sources & evidence

ORD record: ord-2f1cd6e622ce48a991bd7aca901403bf
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

Loading…