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

HRID 644513Notes

Reaction equation

HRID 644513 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].[CH3:19][O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C(NC1C=C(C2C3N(C4C=CC=CC=4)C=NC=3C=C(C#N)C=2)C=CC=1)(=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(O)C.C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:17]=[C:16]([C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([O:20][CH3:19])[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 2734370(3-Methoxyphenyl)boronic acidHCID 112450997-(3-Acetamidophenyl)-5-cyano-1-phenylbenzimidazoleHCID 674856275-Cyano-7-iodo-1-phenylbenzimidazole

Product 1

HCID 111981415-Cyano-7-(3-methoxyphenyl)-1-phenylbenzimidazoleYield 31.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

This was prepared from 5-cyano-7-iodo-1-phenylbenzimidazole (173 mg, 0.5 mmol), toluene (3.0 ml), tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol), 3-methoxyphenylboronic acid (76 mg, 0.5 mmol), ethanol (3.0 ml) and potassium carbonate (138 mg, 1.0 mmol) in a similar manner to 7-(3-acetamidophenyl)-5-cyano-1-phenylbenzimidazole. Purification by a similar procedure afforded the title compound (51 mg, 31%) m/z, 326.5 (M+H)+.

Workup

  1. customPurification by a similar procedure

Sources & evidence

ORD record
ord-a36bb14a996b40bfb37a12a761d3d9f0
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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