(5-Bromofuran-2-yl)methanol → 4-((5-Bromo-2-furyl)methoxy)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203086Notes

Reaction equation

HRID 2203086 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.[Br:22][C:23]1[O:27][C:26]([CH2:28][OH:29])=[CH:25][CH:24]=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[Br:22][C:23]1[O:27][C:26]([CH2:28][O:29][C:2]2[CH:7]=[CH:6][N:5]([C:8]3[CH:9]=[CH:10][C:11]4[N:15]=[C:14]([CH:16]5[CH2:18][CH2:17]5)[N:13]([CH3:19])[C:12]=4[CH:20]=3)[C:4](=[O:21])[CH:3]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 14595701(5-Bromofuran-2-yl)methanolHCID 23665647Potassium tert-butoxideHCID 896909614-Chloro-1-(2-cyclopropyl-1-methyl-1h-benzimidazol-6-yl)-2(1h)-pyridinone

Product 1

HCID 1213862564-((5-Bromo-2-furyl)methoxy)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-oneYield 71.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-chloro-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (150 mg) and (5-bromo-2-furyl)methanol (177 mg) in toluene (2.0 ml) was added potassium tert-butoxide (112 mg) at 100° C., and the mixture was stirred for 30 min. The mixture was quenched with water (2 ml), and the precipitate was collected. The resulting solid was recrystallized from EtOH—H2O to give the title compound (158 mg) as an off-white solid.

Workup

  1. customThe mixture was quenched with water (2 ml)
  2. customthe precipitate was collected
  3. customThe resulting solid was recrystallized from EtOH—H2O

Sources & evidence

ORD record
ord-4cf1213d79e74e8db1fb311ed0041338
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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