Methyl iodide → 3,3-dimethyl-1-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

HRID 82601Notes

Reaction equation

HRID 82601 reaction equation
[H-].[Na+].[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:23]3=[N:24][CH:25]=[CH:26][CH:27]=[C:22]3[C:21]([CH3:29])([CH3:28])[C:20]2=[O:30])=[CH:15][CH:14]=1.[CH3:31]I.[Cl-].[Cl-].[Ca+2]>CN(C=O)C.CO>[CH3:29][C:21]1([CH3:28])[C:22]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[N:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][C:4]3[N:5]([CH3:31])[C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[N:3]=3)=[CH:14][CH:15]=2)[C:20]1=[O:30]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5284359Calcium ChlorideHCID 58577382HCID 58577382, compound

Product 1

HCID 671269323,3-dimethyl-1-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

NaH (17.28 mg) was added to a solution of 1-[4-(1H-benzimidazol-2-yloxy)phenyl]-3,3-dimethyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (40 mg) and MeI (10.13 μl) in DMF(1 mL) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. The reaction mixture was diluted with MeOH and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane) to give 3,3-dimethyl-1-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (35 mg) as white crystals.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-69cfc1ec65a044d980c25e219cf7da83
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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