Benzimidazole → HCID 58911256, compound

HRID 1295815Notes

Reaction equation

HRID 1295815 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-101b1c62dd3e45a78a69c2ccc3242e3f
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Reaction notes

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