N-bromobutanimide → HCID 69024817, compound

HRID 1866943Notes

Reaction equation

HRID 1866943 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][C:18]([F:26])([F:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:12][C:11]2=[O:27])=[CH:6][CH:5]=1.[Br:29]N1C(=O)CCC1=O>C(#N)C>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][C:18]([F:25])([F:26])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[C:12]([Br:29])[C:11]2=[O:27])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69026153HCID 69026153, compound

Product 1

HCID 69024817HCID 69024817, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl-4-[4-[(difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]benzoate (Step 2) (6.74 g, 17.49 mmol) suspended in acetonitrile (100 mL) was cooled in an ice-bath. N-bromosuccinimide (3.27 g, 18.36 mmol) was added. After 1 hour the ice-bath was removed and after an additional 30 minutes the reaction was diluted with acetonitrile (20 mL). The precipitate was collected by filtration to provide the title compound as an off-white solid (6.94 g, 85%). 1H NMR (300 MHz, CDCl3) δ8.20 (d, J=8.7 Hz, 2H), 7.61 (q, J=7.9 Hz, 1H), 7.30 (d, J=8.7 Hz, 2H), 7.02-6.96 (m, 1H), 6.90 (app dt, J=2.4, 9.5 Hz, 1H), 6.14 (s, 1H), 5.28 (s, 2H), 3.98 (s, 3H), 2.00 (s, 3H). ES-HRMS m/z 464.0304 (M+H calcd for C21H16BrF2NO4 requires 464.0301).

Workup

  1. temperaturewas cooled in an ice-bath
  2. customAfter 1 hour the ice-bath was removed and after an additional 30 minutes the reaction
  3. additionwas diluted with acetonitrile (20 mL)
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-e2db3f125a4f477594fc614038b0ab38
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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