Ammonium formate → 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-(difluoromethyl)-3H-imidazo[4,5-c]pyridin-4(5H)-one

HRID 2209005Notes

Reaction equation

C([O:8][C:9]1[C:14]2[N:15]([CH:18]([F:20])[F:19])[CH:16]=[N:17][C:13]=2[CH:12]=[C:11]([C:21]2[CH:22]=[N:23][N:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:25]=2)[N:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.CN(C=O)C.[OH-].[OH-].[Pd+2]>[C:26]([N:24]1[CH:25]=[C:21]([C:11]2[NH:10][C:9](=[O:8])[C:14]3[N:15]([CH:18]([F:19])[F:20])[CH:16]=[N:17][C:13]=3[CH:12]=2)[CH:22]=[N:23]1)([CH3:29])([CH3:27])[CH3:28]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 4-(benzyloxy)-6-(1-tert-butyl-1H-pyrazol-4-yl)-3-(difluoromethyl)-3H-imidazo[4,5-c]pyridine 2.31 (136 mg, 0.342 mmol) in EtOH (2 mL) and DMF (2 mL) was added ammonium formate (265 mg, 4.2 mmol) and Pd(OH)2 on carbon (20 wt. % Pd, 58 mg). The mixture was heated to 55° C. and was stirred for 1 h. The mixture was diluted with DMF (5 mL) and filtered through Celite. The filtrate was concentrated in vacuo to provide 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-(difluoromethyl)-3H-imidazo[4,5-c]pyridin-4(5H)-one 2.33, which was used without further purification.

Workup

filtrationfiltered through Celite
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-f42516c8984e4a37acd0bf9688ef94f9
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Reaction notes

Loading…