Ammonia → 4-(Benzyloxy)-1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203037Notes

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]([CH2:25][CH3:26])[N:22]([CH3:27])[C:21]=2[CH:28]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC.N>[Cu]I.CS(C)=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]([CH2:25][CH3:26])[N:22]([CH3:27])[C:21]=3[CH:28]=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: 150 °C

Procedure

A mixture of 4-(benzyloxy)pyridin-2(1H)-one (1.0 g), 6-bromo-2-ethyl-1-methyl-1H-benzimidazole (1.19 g), potassium carbonate (2.06 g), N,N′-dimethylethylenediamine (0.53 ml), CuI (0.95 g) and DMSO (20 ml) was stirred at 150° C. for 2 h. After cooling to 0° C., 28% NH3 solution (56.0 ml) was added. The precipitate was collected by filtration. The collected material was dissolved in THF, passed through a plug of NH silica gel (EtOAc) and concentrated in vacuo. The resulting solid was collected to give the title compound (1.03 g) as a pink solid.

Workup

temperatureAfter cooling to 0° C.
filtrationThe precipitate was collected by filtration
dissolutionThe collected material was dissolved in THF
concentrationconcentrated in vacuo
customThe resulting solid was collected

Sources & evidence

ORD record: ord-4cd2244d9d8947cf8bc68da82ffc45d6
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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