Boron tribromide → 5-(1-methyl-1H-pyrazol-4-yl)-quinolin-6-ol
Reaction equation
C[O:2][C:3]1[C:4]([C:13]2[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=2)=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.B(Br)(Br)Br>ClCCl>[CH3:18][N:16]1[CH:17]=[C:13]([C:4]2[C:3]([OH:2])=[CH:12][CH:11]=[C:10]3[C:5]=2[CH:6]=[CH:7][CH:8]=[N:9]3)[CH:14]=[N:15]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A flask was charged with compound 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)-quinoline (5.5 g, 0.023 mol) and dichloromethane (50 mL). A solution of boron tribromide (27.6 mL, 1M solution in dichloromethane, 27.6 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes, then the cooling bath was removed and the reaction was stirred for 1.5 hours at room temperature. The reaction was quenched by slowly adding excess 10% aqueous hydrochloric acid, then the solution was basified to pH=6 with 20% aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate and the organic phase was washed with brine, dried over Na2SO4, and filtered. Removal of the solvent gave 4 g of 5-(1-methyl-1H-pyrazol-4-yl)-quinolin-6-ol as a yellow solid.
Workup
- customthe cooling bath was removed
- stirringthe reaction was stirred for 1.5 hours at room temperature
- customThe reaction was quenched by slowly adding excess 10% aqueous hydrochloric acid
- extractionThe mixture was extracted with ethyl acetate
- washthe organic phase was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customRemoval of the solvent
Sources & evidence
- ORD record
- ord-3dd8815221bf40aca7b7dcc1ae9d3787
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507489B2
Reaction notes
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