Sodium Carbonate → 7-(3-Aminophenyl)-1-phenyl-5-trifluoromethylbenzimidazole

HRID 644499Notes

Reaction equation

HRID 644499 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.[NH2:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)CCO>O.C(COC)OC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:21][C:22]1[CH:27]=[C:26]([C:2]2[C:7]3[N:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:9]=[N:10][C:6]=3[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=2)[CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 104421,3-PropanediolHCID 922693-Aminophenylboronic acidHCID 194260247-Iodo-1-phenyl-5-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 114623287-(3-Aminophenyl)-1-phenyl-5-trifluoromethylbenzimidazole

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (3.2 g, 8.2 mmol), 3-aminophenyl boronic acid (1.68 g, 12.3 mmol), sodium carbonate (5.68 g, 41 mmol), 1,3-propanediol (2.94 ml, 41 mmol) and bis(triphenylphosphin)palladium dichloride (200 mg, 0.28 mmol) in a mixture of water (13 ml) and dimethoxyethane (26 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 methanol (99:1, v/v). The product was isolated by removal of solvent from appropriate eluate fractions followed by crystallisation of the residue from 2-propanol (50 ml). Yield: 2.7 g (93%), m/z, 354.1 (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 methanol (99:1
  6. customThe product was isolated by removal of solvent from appropriate eluate fractions
  7. customfollowed by crystallisation of the residue from 2-propanol (50 ml)

Sources & evidence

ORD record
ord-8716852b8a594a40a2d729d2e5d52845
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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