N-bromobutanimide → 4-(benzylamino)-3-bromo-1-(3-fluorobenzyl)pyridin-2(1H)-one

HRID 1866889Notes

Reaction equation

HRID 1866889 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O>C(Cl)Cl>[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[C:10]=1[Br:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22050728HCID 22050728, compound

Product 1

HCID 220506134-(benzylamino)-3-bromo-1-(3-fluorobenzyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(benzylamino)-1-(3-fluorobenzyl)pyridin-2(1H)-one (0.50 g, 1.62 mmol) in anhydrous CH2Cl2 (10 mL) was added N-bromosuccinimide (NBS, 0.30 g, 1.7 mmol). The reaction was stirred at room temperature under a nitrogen atmosphere for 3 h. The reaction mixture was purified by flash chromatography (silica gel) using EtOAc in hexanes (1:1 v/v). The appropriate fractions were combined and concentrated.

Workup

  1. customThe reaction mixture was purified by flash chromatography (silica gel)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-48ba4bc6c2794b799f1d8f68d3f7341f
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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