Ammonium formate → tert-butyl 4-(1-(4-hydroxy-3-methoxybenzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate

HRID 706433Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[O:32]CC1C=NC(OC)=CC=1)[CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:17]=3)=[CH:15][C:10]=2[N:9]=[CH:8]1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:32][C:31]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([CH:16]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[CH2:18][CH2:17]4)=[CH:15][C:10]=3[N:9]=[CH:8]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of tert-butyl 4-(1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-1H-benzo[d]imidazol-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.56 g, 1.00 mmol) in methanol (15 mL) was added ammonium formate (0.63 g, 10 mmol) and palladium on carbon (0.30 g). The reaction mixture was heated to 60° C. under H2. After 16 h, the reaction mixture was allowed to cool to room temperature and was filtered through Celite. The filtrate was concentrated. The residue was purified by silica gel chromatography (5% methanol/dichloromethane elute) to afford 0.42 g (96%) of tert-butyl 4-(1-(4-hydroxy-3-methoxybenzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate as a light yellow solid.

Workup

temperatureto cool to room temperature
filtrationwas filtered through Celite
concentrationThe filtrate was concentrated
customThe residue was purified by silica gel chromatography (5% methanol/dichloromethane elute)

Sources & evidence

ORD record: ord-67341453c46f46d4a248824f72b5c0af
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174986B2

Reaction notes

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