Bromine → 5-(2-bromopropanoyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamide

HRID 559807Notes

Reaction equation

HRID 559807 reaction equation
[Br:1]Br.[CH3:3][C:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[C:8](=[O:20])[C:7]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[O:22])=[CH:6][C:5]=1[C:35](=[O:38])[CH2:36][CH3:37]>C1COCC1>[Br:1][CH:36]([CH3:37])[C:35]([C:5]1[CH:6]=[C:7]([C:21]([NH:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:29][CH:30]=2)=[O:22])[C:8](=[O:20])[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[C:4]=1[CH3:3])=[O:38]

Participants

4

Reactant 2

HCID 24408BromineHCID 667253236-Methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-5-propionyl-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 866147825-(2-bromopropanoyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamideYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bromine (84 μl, 1.61 mmol) in THF (5 ml) was added to a solution of 6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-5-propionyl-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (700 mg, 1.34 mmol) in TEF (10 ml). After 2 h, the yellow colour had disappeared. The reaction mixture was partitioned between water and ethyl acetate, the organic phase was separated, dried and evaporated under reduced pressure to give the title compound (800 mg, 99%).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe organic phase was separated
  3. customdried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5b73081c0af04eeea02dbc55f57dac10
Source dataset
uspto-grants-2011_11
Patent number
US08063073B2

Reaction notes

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