Dimethylformamide → 4-(1-Benzothiophen-5-ylmethoxy)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203082Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (100 mg), benzo[b]thiophen-5-ylmethanol (110 mg), cesium carbonate (326 mg) and DMF (3 ml) was heated at 100° C. overnight. The mixture was poured into water, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (15 mg) as a white solid.

Workup

extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
custompurified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record: ord-9023b02b03ce4789bbaca7cb32156fc0
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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