Potassium Carbonate → 5-Cyano-7-(3-hydroxymethylphenyl)-1-phenylbenzimidazole

HRID 644510Notes

Reaction equation

HRID 644510 reaction equation
[C:1]([C:3]1[CH:17]=[C:16](I)[C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2].[OH:19][CH2:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].ClCCl.CO>C1(C)C=CC=CC=1.C(O)C.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:1]([C:3]1[CH:17]=[C:16]([C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:20][OH:19])[CH:26]=2)[C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 21226129Dichloromethane methanolHCID 674856275-Cyano-7-iodo-1-phenylbenzimidazole

Product 1

HCID 113931985-Cyano-7-(3-hydroxymethylphenyl)-1-phenylbenzimidazole

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

5-Cyano-7-iodo-1-phenylbenzimidazole (1.0 g, 2.90 mmol), 3-hydroxymethyl-phenylboronic acid (440 mg, 2.90 mmol) and tetrakis(triphenylphosphine)palladium(0) (330 mg, 2.90 mmol) were dissolved in toluene (8.0 ml) and ethanol (2.0 ml). Potassium carbonate (2M in water, 2.9 ml, 800 mg, 5.8 mmol) was added and the reaction mixture heated at reflux under a nitrogen atmosphere for 16 h. The reaction mixture was passed through a plug of silica gel using dichloromethane/methanol (19:1) to elute. The organic phase was concentrated under reduced pressure and the resultant gum triturated with ethyl acetate and dichloromethane. 5-Cyano-7-(3-hydroxymethylphenyl)-1-phenylbenzimidazole was obtained as an off-white solid (500 mg, 39%) m/z, 326.2 (M+H)+.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux under a nitrogen atmosphere for 16 h
  3. washto elute
  4. concentrationThe organic phase was concentrated under reduced pressure
  5. customthe resultant gum triturated with ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-60b5929cf7824ecb957ad3c4456c0af2
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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