Ammonia → 1-(1,2-Dimethyl-1H-benzimidazol-6-yl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one

HRID 2203081Notes

Reaction equation

HRID 2203081 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1.[F:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][NH:23][C:22](=[O:26])[CH:21]=2)=[CH:16][CH:15]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+].N>[Cu]I.CS(C)=O>[CH3:11][N:7]1[C:6]2[CH:12]=[C:2]([N:23]3[CH:24]=[CH:25][C:20]([O:19][CH2:18][C:17]4[CH:27]=[CH:28][C:14]([F:13])=[CH:15][CH:16]=4)=[CH:21][C:22]3=[O:26])[CH:3]=[CH:4][C:5]=2[N:9]=[C:8]1[CH3:10]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-oneHCID 581095096-bromo-1,2-dimethyl-1H-benzo[d]imidazole

Product 1

HCID 716609171-(1,2-Dimethyl-1H-benzimidazol-6-yl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-oneYield 24.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-bromo-1,2-dimethyl-1H-benzimidazole (500 mg), 4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (487 mg), CuI (423 mg), N,N′-dimethyl-1,2-ethanediamine (0.236 ml), potassium carbonate (921 mg) and DMSO (10 ml) was stirred at 150° C. for 1 h. 28% NH3 solution was added to the resulting mixture, and the solid was washed with water. The solid was purified by NH silica gel column chromatography (hexane/EtOAc), followed by recrystallization from EtOAc-hexane to give the title compound (200 mg) as a white solid.

Workup

  1. washthe solid was washed with water
  2. customThe solid was purified by NH silica gel column chromatography (hexane/EtOAc)
  3. customfollowed by recrystallization from EtOAc-hexane

Sources & evidence

ORD record
ord-5609f6dd009b4e69adba33d19c313c86
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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