N-bromobutanimide → HCID 22051179, compound

HRID 1866954Notes

Reaction equation

HRID 1866954 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([N:9]2[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[CH:11][C:10]2=[O:26])[CH:6]=[CH:7][CH:8]=1.[Br:27]N1C(=O)CCC1=O>C(#N)C>[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([N:9]2[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[C:11]([Br:27])[C:10]2=[O:26])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22050057HCID 22050057, compound

Product 1

HCID 22051179HCID 22051179, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-[3-(aminomethyl)phenyl]-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one from step 3 (3.89 g, 10.93 mmol) suspended in acetonitrile (42 mL) was cooled in an ice-bath. N-bromosuccinimide (2.04 g, 11.47 mmol) was added and the ice-bath was removed. The reaction mixture was stirred for 1.5 hours at room temperature. The reaction was diluted with acetonitrile (100 mL) and the precipitate that formed was collected by filtration and washed with acetonitrile (3×30 mL) to afford an off-white solid (2.74 g, 58%). 1H NMR (400 MHz, DMSO-d6) δ 7.67-7.59 (m, 3H), 7.34-7.31 (m, 2H), 7.04 (app t, J=8.72 Hz, 2H), 7.05-6.88 (m, 2H), 6.13 (s, 1H), 5.30 (s, 2H), 3.95 (s, 1H), 2.01 (s, 3H). ES-HRMS m/z 435.0538 (M+H C20H17BrF2N2O2 requires 435.0514).

Workup

  1. temperaturewas cooled in an ice-bath
  2. customthe ice-bath was removed
  3. additionThe reaction was diluted with acetonitrile (100 mL)
  4. customthe precipitate that formed
  5. filtrationwas collected by filtration
  6. washwashed with acetonitrile (3×30 mL)

Sources & evidence

ORD record
ord-cb3b806cff584d5a8fb953d1b2c3750e
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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