2-(1-Azidoethyl)-3-phenyl-3H-imidazo[4,5-c]pyridine → 1-(3-Phenyl-3H-imidazo[4,5-c]pyridin-2-yl)ethylamine

HRID 243047Notes

Reaction equation

[N:1]([CH:4]([C:6]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:8]=2[N:7]=1)[CH3:5])=[N+]=[N-]>[Pd].CCOC(C)=O>[C:15]1([N:14]2[C:9]3[CH:10]=[N:11][CH:12]=[CH:13][C:8]=3[N:7]=[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)-3-phenyl-3H-imidazo[4,5-c]pyridine (0.89 g, 3.39 mmol) and 10% palladium on carbon (0.20 g) in EtOAc (40 mL) was stirred under an atmosphere of hydrogen at atmospheric pressure and 20° C. for 3 h. The catalyst was removed by filtration and the filtrate concentrated in vacuo. The resulting residue was purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM) to give the title compound as a white solid (0.53 g, 65%). LCMS (method H): Rt 0.25 min, [M+H]+ 239.

Workup

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

Sources & evidence

ORD record: ord-a31ade20ca8747e0aa969eb5b1ae0d0a
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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