Sodium hydride → 4-[(2-Bromo-4-thiazolyl)methoxy]-1-(2-cyclopropyl-1-methyl-1h-benzimidazol-6-yl)-2(1h)-pyridinone

HRID 2203112Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2-bromo-1,3-thiazol-4-yl)methanol (169 mg) in DMA (5 ml) was added NaH (60% in oil, 34.9 mg) at 0° C. After being stirred at 0° C. for 30 min, 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one was added to the reaction mixture, and the mixture was stirred at 120° C. under N2 atmosphere for 30 min. The reaction mixture was quenched with water and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (57.0 mg) as a white solid.

Workup

stirringthe mixture was stirred at 120° C. under N2 atmosphere for 30 min
customThe reaction mixture was quenched with water
extractionextracted with EtOAc
washThe extract was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
custompurified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record: ord-2b83714397b64e35bde56e73cdb92fb5
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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