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Sodium hydride → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(pentafluoroethyl)-1,3-thiazol-4-yl) methoxy)pyridin-2(1H)-one

HRID 2203107
Notes
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Reaction equation

HRID 2203107 reaction equation
[H-].[Na+].[F:3][C:4]([F:16])([C:9]1[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1)[C:5]([F:8])([F:7])[F:6].Br[C:18]1[CH:23]=[CH:22][N:21]([C:24]2[CH:25]=[CH:26][C:27]3[N:31]=[C:30]([CH:32]4[CH2:34][CH2:33]4)[N:29]([CH3:35])[C:28]=3[CH:36]=2)[C:20](=[O:37])[CH:19]=1>CC(N(C)C)=O>[CH:32]1([C:30]2[N:29]([CH3:35])[C:28]3[CH:36]=[C:24]([N:21]4[CH:22]=[CH:23][C:18]([O:15][CH2:14][C:12]5[N:13]=[C:9]([C:4]([F:3])([F:16])[C:5]([F:8])([F:7])[F:6])[S:10][CH:11]=5)=[CH:19][C:20]4=[O:37])[CH:25]=[CH:26][C:27]=3[N:31]=2)[CH2:33][CH2:34]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 54209966(2-(Perfluoroethyl)thiazol-4-yl)methanolHCID 896908634-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

Product 1

HCID 896912031-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(pentafluoroethyl)-1,3-thiazol-4-yl) methoxy)pyridin-2(1H)-oneYield 5.9%

Reagents, catalysts & solvents 1

HCID 31374
Dimethylacetamide
Solvent

Conditions

Temperature
0 °C

Procedure

NaH (60% in oil, 51.5 mg) was added to a solution of (2-(perfluoroethyl)thiazol-4-yl)methanol (300 mg) in DMA (5 ml) at 0° C. After being stirred at 0° C. for 30 min, 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzo[d]imidazol-6-yl)pyridin-2(1H)-one (295 mg) was added to the reaction mixture. The mixture was stirred at 120° C. under N2 atmosphere for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc), followed by crystallization from EtOH-water to give the title compound (25 mg) as a white solid.

Workup

  1. stirringThe mixture was stirred at 120° C. under N2 atmosphere for 1 h
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water and brine successively
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)
  9. customfollowed by crystallization from EtOH-water

Sources & evidence

ORD record
ord-3378319c6142478eb3ad1d89d892dbdd
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365540B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes