Benzimidazole → HCID 58911256, compound

HRID 2358244Notes

Reaction equation

HRID 2358244 reaction equation
O[CH2:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:12].[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][CH:14]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>C(#N)C>[N:13]1([CH2:2][N:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]2=[O:12])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 24206546HCID 24206546, compound

Product 1

HCID 58911256HCID 58911256, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one a25 (1 eq, 3.06 mmol, 500 mg), benzimidazole (4 eq, 12.26 mmol, 1.45 g) and carbonyldiimidazole (1 eq, 3.06 mmol, 500 mg) in acetonitrile (3 ml) was irradiated in a microwave apparatus (CEM discover) for 10 minutes (100 w). After evaporation of the acetonitrile under reduced pressure, the crude product was purified by preparative HPLC on reverse phase to give 203 mg of 1-(1H-benzimidazol-1-ylmethyl)-1,3-dihydro-2H-indol-2-one 167 (25%) after recrystallization in diisopropylether.

Workup

  1. customAfter evaporation of the acetonitrile under reduced pressure
  2. customthe crude product was purified by preparative HPLC on reverse phase

Sources & evidence

ORD record
ord-8f9575dcf21344f3a9aa43048bd59713
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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