Bromine → 2-Bromo-1-(6-methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone
Reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8](=[O:20])[CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:4][CH:3]=1.[Br:21]Br>C(O)(=O)C>[Br:21][CH:9]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[CH:13]2)[C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)=[O:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1-(6-methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone of Step C (1.13 g, 4.3 mmol) in acetic acid (40 mL) was slowly added a solution of bromine (0.22 ml, 4.3 mmol, 1 equiv) in acetic acid (5 mL) over 2 minutes. After stirring at the ambient temperature for 3 hours the reaction mixture was concentrated in vacuo, and the residue was triturated with a mixture of ethyl acetate (20 mL) and ether (20 mL). The crude hydrobromide was converted to the free base by treating with saturated aqueous sodium hydrogen carbonate. The product was extracted with ethyl acetate, the combined organics were washed with saturated aqueous sodium chloride and concentrated in vacuo. Silica gel chromatography (9:1 methylene chloride/acetonitrile) provided title compound as a yellow oil (0.95 g).
Workup
- concentrationwas concentrated in vacuo
- customthe residue was triturated with a mixture of ethyl acetate (20 mL) and ether (20 mL)
- additionby treating with saturated aqueous sodium hydrogen carbonate
- extractionThe product was extracted with ethyl acetate
- washthe combined organics were washed with saturated aqueous sodium chloride
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-78098e51e95e4102b98658fc8bf856db
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07417041B2
Reaction notes
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