N-bromobutanimide → HCID 22050757, compound

HRID 1832020Notes

Reaction equation

HRID 1832020 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:11](=[O:23])[CH:10]=2)=[O:7])=[CH:4][CH:3]=1.C1C(=O)N([Br:33])C(=O)C1>C(#N)C>[Br:33][C:10]1[C:11](=[O:23])[N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[CH:13]=[CH:14][C:9]=1[NH:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22051083HCID 22051083, compound

Product 1

HCID 22050757HCID 22050757, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-fluoro-N-[1-(3-fluorobenzyl)-2-oxo-1,2-dihydropyridin-4-yl]benzamide (0.305 g, 0.89 mmol) in acetonitrile (7 mL) was added NBS (0.159 g, 0.89 mmol). The reaction mixture stirred at room temperature for 1.5 hours. The filtrate was removed under reduced pressure and the residue was purified by flash column chromatography (ethyl acetate/hexane 1:1 v/v). The fractions were concentrated. 1H-NMR (CD3OD, 400 MHz) δ 8.03 (m, 2H), 7.79 (d, 1H, J=7.6 Hz), 7.47 (d, 1H, J=8.0 Hz), 7.28 (m, 3H), 7.12 (m, 3H), 5.23 (s, 2H); ES-HRMS m/z 419.0202/421.0191 (M+H calculated for C19H14N2O2F2Br requires 419.0201/421.0183).

Workup

  1. customThe filtrate was removed under reduced pressure
  2. customthe residue was purified by flash column chromatography (ethyl acetate/hexane 1:1 v/v)
  3. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-47ab64e02ba7466ba0f48882717377ef
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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