Potassium Carbonate → 5-Cyano-7-(4-hydroxymethylphenyl)-1-phenylbenzimidazole

HRID 644525Notes

Reaction equation

HRID 644525 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:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].C(C1C=C(C2C=CC=C(CO)C=2)C2N(C3C=CC=CC=3)C=NC=2C=1)#N>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:24]2[CH:25]=[CH:26][C:21]([CH2:20][OH:19])=[CH:22][CH:23]=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 27347064-(Hydroxymethyl)benzeneboronic acidHCID 113931985-Cyano-7-(3-hydroxymethylphenyl)-1-phenylbenzimidazoleHCID 674856275-Cyano-7-iodo-1-phenylbenzimidazole

Product 1

HCID 674850065-Cyano-7-(4-hydroxymethylphenyl)-1-phenylbenzimidazole

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

5-Cyano-7-(4-hydroxymethylphenyl)-1-phenylbenzimidazole was prepared from 5-cyano-7-iodo-1-phenylbenzimidazole (1.0 g, 2.90 mmol), 4-hydroxymethylphenylboronic acid (440 mg, 2.90 mmol), tetrakis(triphenylphosphine)palladium(0) (330 mg, 2.90 mmol) and potassium carbonate (2M in water, 2.9 ml, 800 mg, 5.8 mmol) in toluene (8.0 ml) and ethanol (2.0 ml) using the method described for 5-cyano-7-(3-hydroxymethylphenyl)-1-phenylbenzimidazole. 5-Cyano-7-(4-hydroxymethylphenyl)-1-phenylbenzimidazole was obtained as a white solid (711 mg) m/z, 326.3 (M+H)+.

Sources & evidence

ORD record
ord-3ac02db958504ecb8d09ec5b60bffbc2
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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