Boron tribromide → HCID 56847213, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][C:10]([C:12]2[C:13](=[O:31])[N:14]([CH2:27][CH2:28][O:29]C)[C:15]3[C:20]([C:21]=2[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=3)=[O:11])[CH:5]=[CH:6][CH:7]=1.BrB(Br)Br.CCOC(C)=O.CCCCCC>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][C:10]([C:12]2[C:13](=[O:31])[N:14]([CH2:27][CH2:28][OH:29])[C:15]3[C:20]([C:21]=2[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:25])([F:26])[F:24])[CH:16]=3)=[O:11])[CH:5]=[CH:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 800 mg (1.83 mmol) N-[(3-fluorophenyl)-methyl]-1-(2-methoxy-ethyl)-4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylic acid amide (example 4) in DCM (30 ml) was added 0.26 ml (2.7 mmol) tribromoborane at −78° C. The reaction mixture was stirred at 0° C. for 2 h. Then the reaction mixture was cooled to −78° C. and quenched with a sat. NaHCO3 sol. The reaction mixture was diluted with DCM (20 ml) and washed with a sat. NaHCO3 sol. (20 ml), brine (20 ml), and water (20 ml), dried over Na2SO4 and concentrated in vacuum. After CC (EtOAc/hexane 1:4) of the residue, 750 mg (1.77 mmol, 97%) N-[(3-Fluorophenyl)-methyl]-1-(2-hydroxy-ethyl)-4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylic acid amide (example 38) were obtained. MS: m/z 423.1 [M+H]+.
Workup
- temperatureThen the reaction mixture was cooled to −78° C.
- customquenched with a sat. NaHCO3 sol. The reaction mixture
- additionwas diluted with DCM (20 ml)
- washwashed with a sat. NaHCO3 sol. (20 ml), brine (20 ml), and water (20 ml)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuum
Sources & evidence
- ORD record
- ord-c2e305ee190c4739b9ec362f95f9a112
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653102B2
Reaction notes
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