Sodium hydride → 3-(2'-cyano-1,1'-biphenyl-4-yl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

HRID 36104Notes

Reaction equation

HRID 36104 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:9]=[C:8]2[NH:10][C:11]([CH2:13][CH3:14])=[N:12][C:7]2=[C:6]([CH3:15])[CH:5]=1.Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])=[CH:20][CH:19]=1>CN(C=O)C>[C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:21]1[CH:20]=[CH:19][C:18]([CH2:17][N:10]2[C:8]3=[N:9][C:4]([CH3:3])=[CH:5][C:6]([CH3:15])=[C:7]3[N:12]=[C:11]2[CH2:13][CH3:14])=[CH:23][CH:22]=1)#[N:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 178437439HCID 178437439, compound

Product 1

HCID 152363243-(2'-cyano-1,1'-biphenyl-4-yl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% NaH (400 mg) in DMF (10 mL) was added the solution of 5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine (1.75 g, 10 mmol) DMF (10 mL) at 0° C. After 5 min, 4-bromomethyl-2'-cyano-1,1'-biphenyl (2.72 g, 10 mmol; Eur. Pat. Appl. 324,377, 1989) in DMF (10 mL) was added at 0° C. and the mixture was stirred at rt for 15 hrs. Extractive workup (2×EtOAc) from water followed by purification of the concentrated organic phases (Si02,) gave 3-(2'-cyano-1,1'-biphenyl-4-yl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine as a solid.

Workup

  1. customExtractive workup (2×EtOAc) from water followed by purification of the concentrated organic phases (Si02,)

Sources & evidence

ORD record
ord-5dc27ccf3efc4b41a3a91ee7cbe9bc79
Source dataset
uspto-grants-1995_05
Patent number
US05412097

Reaction notes

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