Ammonia → 4-(benzyloxy)-1-(1,2-dimethyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203121Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[CH:18]=[CH:19][C:20]2[N:24]=[C:23]([CH3:25])[N:22]([CH3:26])[C:21]=2[CH:27]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+].N>CS(C)=O.[Cu]I.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:17]2[CH:18]=[CH:19][C:20]3[N:24]=[C:23]([CH3:25])[N:22]([CH3:26])[C:21]=3[CH:27]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 4-benzyloxy-2(1H)-pyridone (21.5 g), 6-bromo-1,2-dimethyl-1H-benzo[d]imidazole (16 g), N,N′-dimethylethylenediamine (7.57 ml) and potassium carbonate (29.5 g) in DMSO (160 ml) was added CuI (13.5 g), and the mixture was stirred at 90° C. for 5 h under Ar atmosphere. After the mixture was cooled, 28% NH3 solution (160 ml) and water (160 ml) were added. The precipitate was collected by filtration, washed with water and diisopropyl ether successively, and dried to give a solid. The residue was purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH) to give the title compound (14.5 g) as an off-white solid.

Workup

temperatureAfter the mixture was cooled
filtrationThe precipitate was collected by filtration
washwashed with water and diisopropyl ether successively
customdried
customto give a solid
customThe residue was purified by silica gel column chromatography (hexane/EtOAc

Sources & evidence

ORD record: ord-8c688483617946759b2d70be31344717
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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