N-bromobutanimide → HCID 22050663, compound

HRID 1867033Notes

Reaction equation

HRID 1867033 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:12]([CH3:13])=[CH:11][C:10]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[CH:9][C:8]2=[O:23])=[CH:4][CH:3]=1.C1C(=O)N([Br:33])C(=O)C1>C(Cl)Cl>[Br:33][C:9]1[C:8](=[O:23])[N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:25][CH:24]=2)[C:12]([CH3:13])=[CH:11][C:10]=1[NH:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22051128HCID 22051128, compound

Product 1

HCID 22050663HCID 22050663, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(4-fluorobenzyl)-4-[(4-fluorobenzyl)amino]-6-methylpyridin-2(1H)-one (0.2857 g, 0.84 mmol) in MeCl2 was added NBS (0.156 g, 0.88 mmol). The reaction stirred at room temperature under nitrogen for 45 minutes. The reaction mixture was diluted with MeCl2 and washed with NaHCO3. The organic extracts were washed with water, dried over Na2SO4, and concentrated to afford the desired product (0.3242 g, 92%) as a yellow solid. 1H-NMR (CD3OD, 400 MHz) δ 7.32 (q, 2H), 7.04 (m, 6H), 5.91 (s, 1H), 5.28 (s, 2H), 4.50 (s, 2H), 2.17 (s, 3H); ES-HRMS m/z 419.0549/421.0537 (M+H calculated for C20H18N2OBrF2 requires 419.0565/421.0547).

Workup

  1. washwashed with NaHCO3
  2. washThe organic extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-451f6c35613e4af4976ac2adee117cb3
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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