Bromine → 5-[bromo(4-chlorophenyl)acetyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

HRID 1672609Notes

Reaction equation

HRID 1672609 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[CH:14]=[C:15]([C:31]([NH:33][CH3:34])=[O:32])[C:16](=[O:30])[N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:18]=2[CH3:19])=[O:12])=[CH:6][CH:5]=1>C(O)(=O)C.C1COCC1>[Br:1][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=1)[C:11]([C:13]1[CH:14]=[C:15]([C:31]([NH:33][CH3:34])=[O:32])[C:16](=[O:30])[N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[C:18]=1[CH3:19])=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 673426465-[(4-chlorophenyl)acetyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 866304695-[bromo(4-chlorophenyl)acetyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamideYield 98%

Reagents, catalysts & solvents 1

HCID 23444217Acetic acid tetrahydrofuranSolvent

Procedure

A solution of bromine (30 mg, 19 mmol) in acetic acid—THF was added dropwise to a solution of 5-[(4-chlorophenyl)acetyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (75 mg, 0.162 mmol). After the addition, stirring was continued at RT overnight. The solvents were removed and the residue was purified on an Xterra C8 column using a gradient of acetonitrile/water. Freeze drying of the mixture afforded the title compound (86 mg, 95%).

Workup

  1. additionAfter the addition
  2. customThe solvents were removed
  3. customthe residue was purified on an Xterra C8 column
  4. customFreeze drying of the mixture

Sources & evidence

ORD record
ord-088fda0c0a6a46dc8da5410138c7095a
Source dataset
uspto-grants-2011_08
Patent number
US07998984B2

Reaction notes

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