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

HRID 1886462Notes

Reaction equation

HRID 1886462 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+].Br[CH2:27][C:28]1[C:29]([C:34]#[N:35])=[CH:30][CH:31]=[CH:32][CH:33]=1>CN(C=O)C>[C:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:27][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)#[N:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 895992-(Bromomethyl)benzonitrileHCID 100407273-(5-indolyl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 102515203-[N-(2-cyanobenzyl)-5-indolyl]methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of Example 2, Step A, (75 mg, 0.25 mmol) in 3 mL of DMF was added 11 mg (0.27 mmol, 1.1 eq) of 60% NaH followed by α-bromo-o-tolunitrile (58 mg, 0.30 mmol, 1.2 eq). The mixture was stirred for 16 hours and then concentrated in vacuo. The resultant oil was flash chromatographed with 1:1 hexane/ethyl acetate to yield the titled compound (98 mg, 95%).

Workup

  1. concentrationconcentrated in vacuo
  2. customchromatographed with 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-ad09137512a244b8a08fd4be46f14853
Source dataset
uspto-grants-1992_09
Patent number
US05151435

Reaction notes

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