N-bromobutanimide → 2-(5-Bromo-1-methylimidazol-4-yl)pyridine-4-carbonitrile

HRID 2277439Notes

Reaction equation

HRID 2277439 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][N:8]=2)[N:4]=[CH:3]1.[Br:15]N1C(=O)CCC1=O>ClCCl>[Br:15][C:6]1[N:2]([CH3:1])[CH:3]=[N:4][C:5]=1[C:7]1[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 904075092-(1-Methylimidazol-4-yl)pyridine-4-carbonitrile

Product 1

HCID 904081442-(5-Bromo-1-methylimidazol-4-yl)pyridine-4-carbonitrileYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1-methyl-1H-imidazol-4-yl)pyridine-4-carbonitrile (100 mg, 0.54 mmol) in dichloromethane (5 mL) was added N-bromosuccinimide (102 mg, 0.57 mmol). The reaction mixture was stirred at r.t. for 3 hrs. It was then purified by flash column chromatography (EtOAc/Hexane) to afford 2-(5-bromo-1-methyl-1H-imidazol-4-yl)pyridine-4-carbonitrile (140 mg, quantitative yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 3.67 (3H, s), 7.70 (1H, d, J=4.8 Hz), 8.04 (1H, s), 8.19 (1H, s), 8.81 (1H, d, J=4.2 Hz). [M+H] Calc'd for C10H7BrN4, 264. Found, 263, 265.

Workup

  1. customIt was then purified by flash column chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-fca2c45d45194c2f837676f646700f46
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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