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Toluene → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(trifluoromethyl)-1,3-thiazol-4-yl)methoxy)pyridin-2(1H)-one

HRID 2203093
Notes
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Reaction equation

HRID 2203093 reaction equation
Br[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.[F:22][C:23]([F:32])([F:31])[C:24]1[S:25][CH:26]=[C:27]([CH2:29][OH:30])[N:28]=1.C1(C)C=CC=CC=1.CC(C)([O-])C.[K+]>O>[CH:16]1([C:14]2[N:13]([CH3:19])[C:12]3[CH:20]=[C:8]([N:5]4[CH:6]=[CH:7][C:2]([O:30][CH2:29][C:27]5[N:28]=[C:24]([C:23]([F:32])([F:31])[F:22])[S:25][CH:26]=5)=[CH:3][C:4]4=[O:21])[CH:9]=[CH:10][C:11]=3[N:15]=2)[CH2:18][CH2:17]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1140TolueneHCID 20079604[2-(Trifluoromethyl)-1,3-thiazol-4-yl]methanolHCID 23665647Potassium tert-butoxideHCID 896908634-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

Product 1

HCID 897022641-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(trifluoromethyl)-1,3-thiazol-4-yl)methoxy)pyridin-2(1H)-one
Yield 22.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (100 mg), (2-(trifluoromethyl)thiazol-4-yl)methanol (80 mg) and toluene (5 ml) was added potassium tert-butoxide (98 mg) at 100° C., and the mixture was stirred at the same temperature overnight. The mixture was poured into water, and extracted with EtOAc. The extract 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 (29.0 mg) as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-ef3451a9f6744524967fa48bbf7f0f20
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365540B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes