Methanol → 4-(5-Fluoro-2-hydroxyphenyl)-4-methyl-2-trifluoromethyl-1-(2-(trifluoromethyl)-quinolin-5-ylamino)pentan-2-ol
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:34]C)=[C:6]([C:8]([CH3:33])([CH3:32])[CH2:9][C:10]([C:28]([F:31])([F:30])[F:29])([OH:27])[CH2:11][NH:12][C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][C:17]([C:23]([F:26])([F:25])[F:24])=[N:18]3)[CH:7]=1.B(Br)(Br)Br.CO>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:34])=[C:6]([C:8]([CH3:32])([CH3:33])[CH2:9][C:10]([C:28]([F:29])([F:30])[F:31])([OH:27])[CH2:11][NH:12][C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][C:17]([C:23]([F:26])([F:24])[F:25])=[N:18]3)[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
100 mg (0.20 mmol) of 4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-1-(2-(trifluoromethyl)quinolin-5-ylamino)pentan-2-ol in 2.0 ml of dichloromethane is mixed at room temperature with 4.0 ml (4.0 mmol) of a 1 M boron tribromide solution. After 20 hours at room temperature, the reaction is brought to a halt by adding 20 ml of methanol. The reaction mixture is allowed to stir for 30 minutes at room temperature, and then the solvent is removed in a vacuum. After chromatography on silica gel with hexane-ethyl acetate (0–100%), 79 mg (80% of theory) of the product is obtained.
Workup
- customthe solvent is removed in a vacuum
- customAfter chromatography on silica gel with hexane-ethyl acetate (0–100%), 79 mg (80% of theory) of the product is obtained
Sources & evidence
- ORD record
- ord-75776e31eda74dbea641e4bb22af57fb
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109212B2
Reaction notes
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