Potassium Carbonate → 1,7-Diphenyl-5-trifluoromethylbenzimidazole

HRID 644501Notes

Reaction equation

HRID 644501 reaction equation
I[C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:11]1([N:8]2[C:7]3[C:2]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:3][C:4]([C:17]([F:20])([F:19])[F:18])=[CH:5][C:6]=3[N:10]=[CH:9]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 194260247-Iodo-1-phenyl-5-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 114731961,7-Diphenyl-5-trifluoromethylbenzimidazoleYield 47.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (370 mg, 1 mmol), benzeneboronic acid (180 mg, 1.5 mmol), potassium carbonate (700 mg, 5 mmol) and tetrakis(triphenylphosphine)palladium(0) (29 mg, 0.025 mmol) in a mixture of water (5 ml) and dimethoxyethane (10 ml) was stirred at reflux overnight. The cooled mixture was partitioned between water and ethyl acetate. The organic phase was collected, washed with brine, dried and concentrated under reduced pressure. Recrystallisation from methanol afforded the product as an off-white solid (160 mg, 47%), m/z, 339.1 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. customThe cooled mixture was partitioned between water and ethyl acetate
  3. customThe organic phase was collected
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-d24d965587a84135b01882fa3493432b
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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