Sodium hydride → 3-[N-(2-cyanobenzoyl)-5-indolyl]methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

HRID 1886460Notes

Reaction equation

HRID 1886460 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]4[N:13]=[C:12]3[CH2:22][CH3:23])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[C:26]([C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31])#[N:27]>CN(C=O)C>[C:26]([C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]4[N:13]=[C:12]3[CH2:22][CH3:23])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)=[O:31])#[N:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1196812-Cyanobenzoyl chlorideHCID 100407273-(5-indolyl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 100258733-[N-(2-cyanobenzoyl)-5-indolyl]methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridineYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of Example 2, Step A (250 mg, 0.82 mmol) in 3 mL of DMF was added 60% NaH (39 mg, 1 mmol, 1.2 eq). After stirring for 5 minutes, 2-cyanobenzoyl chloride (204 mg, 1.23 mmol, 1.5 eq) was added to the reaction mixture. The resultant solution was stirred for 16 hours and the DMF removed in vacuo. The resultant oil was flash chromatographed with 2:1 hexane/ethyl acetate to yield the titled compound (292 mg, 82%).

Workup

  1. customthe DMF removed in vacuo
  2. customchromatographed with 2:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-abd90ae7c0fb4856ae52ad94358102ad
Source dataset
uspto-grants-1992_09
Patent number
US05151435

Reaction notes

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