1-Bromopropane → 2-(1-propyl-1H-imidazol-4-yl)pyridine-4-carbonitrile

HRID 2277474Notes

Reaction equation

HRID 2277474 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][N:7]=2)[N:3]=[CH:2]1.[H-].[Na+].Br[CH2:17][CH2:18][CH3:19]>CN(C=O)C>[CH2:17]([N:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][N:7]=2)[N:3]=[CH:2]1)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 178510201HCID 178510201, compound

Product 1

HCID 904073052-(1-propyl-1H-imidazol-4-yl)pyridine-4-carbonitrileYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(1H-imidazol-4-yl)pyridine-4-carbonitrile (90 mg, 0.53 mmol) in anhydrous DMF (2 mL) was cooled in an ice-water bath. Sodium hydride (60%, 32 mg, 0.8 mmol) was added carefully at 0° C. The reaction mixture was stirred for 10 minutes, after which 1-bromopropane (73 μL, 0.8 mmol) was added. The reaction mixture was warmed up to r.t. and stirred for 1 hr and it was then purified by ISCO flash column (MeOH/DCM=0-5%). 80 mg title compound was obtained as white solid (71%). [M+H] Calc'd for C12H12N4, 213. Found, 213.

Workup

  1. stirringstirred for 1 hr
  2. customit was then purified by ISCO flash column (MeOH/DCM=0-5%)

Sources & evidence

ORD record
ord-8ee26569393f41289da743e7d9a306b3
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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