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

HRID 1888811Notes

Reaction equation

HRID 1888811 reaction equation
BrBr.[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)[CH2:36][CH3:37]>C1COCC1>[CH3:7][C:8]1[O:20][C:36]([CH3:37])=[C:35]([C:5]2[CH:6]=[C:7]([C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:27][CH:26]=3)=[O:22])[C:8](=[O:20])[N:9]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[CH:11]=3)[C:4]=2[CH3:3])[N:9]=1

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 667253385-(2,5-Dimethyl-1,3-oxazol-4-yl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamideYield 213.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 THF (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-8ffdca2a1938414784335501d08faf2e
Source dataset
uspto-grants-2013_08
Patent number
US08501784B2

Reaction notes

Loading…