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

HRID 1832013Notes

Reaction equation

HRID 1832013 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 hours. The reaction mixture was purified by flash chromatography (silica gel) using ethyl acetate in hexane (1:1 v/v). The appropriate fractions were combined and concentrated. 1H-NMR (CD3OD, 400 MHz) δ 7.41 (d, 1H, J=7.6 Hz), 7.31 (m, 6H), 7.04 (m, 3H), 5.99 (d, 1H, J=7.6 Hz), 5.08 (s, 2H), 4.53 (s, 2H); ES-HRMS m/z 387.0508 (M+H calculated for C19H17N2OBrF requires 387.0504).

Workup

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

Sources & evidence

ORD record
ord-e2cfa5cf1287446286eff0c615b71c94
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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