Ethanol → 1-Phenyl-7-(3-pyridyl)-5-trifluoromethylbenzimidazole

HRID 644500Notes

Reaction equation

HRID 644500 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(B(CC)[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)C.C(=O)(O)[O-].[Na+].C(O)C>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:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=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

8

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 6428513-(Diethylboryl)pyridineHCID 194260247-Iodo-1-phenyl-5-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 112330661-Phenyl-7-(3-pyridyl)-5-trifluoromethylbenzimidazole

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (370 mg, 1 mmol), diethyl 3-pyridylborane (220 mg, 1.5 mmol), sodium bicarbonate (420 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 reaction mixture was partitioned between ethyl acetate and water, and the organic extract was purified by column chromatography on silica gel eluting with a mixture of dichloromethane and acetone (9:1, v/v). The product was isolated by removal of solvent from appropriate eluate fractions followed by trituration of the residue with a mixture of water and ethanol. Yield: 130 mg (38%), m/z, 340.1 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. customThe cooled reaction mixture
  3. customwas partitioned between ethyl acetate and water
  4. extractionthe organic extract
  5. customwas purified by column chromatography on silica gel eluting with a mixture of dichloromethane and acetone (9:1
  6. customThe product was isolated by removal of solvent from appropriate eluate fractions

Sources & evidence

ORD record
ord-989d0b38d3c84a67a6bb687d698a346c
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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