4-(5-Fluoro-2-methoxyphenyl)-1-(isoquinolin-1-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol → 4-(5-Fluoro-2-hydroxyphenyl)-1-(isoquinoline-1-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol

HRID 2182641Notes

Reaction equation

HRID 2182641 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:30]C)=[C:6]([C:8]([CH3:29])([CH3:28])[CH2:9][C:10]([C:24]([F:27])([F:26])[F:25])([OH:23])[CH2:11][NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][N:14]=2)[CH:7]=1.B(Br)(Br)Br.C(Cl)Cl>CCCCCC.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:30])=[C:6]([C:8]([CH3:28])([CH3:29])[CH2:9][C:10]([C:24]([F:25])([F:26])[F:27])([OH:23])[CH2:11][NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][N:14]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 219488124-(5-Fluoro-2-methoxyphenyl)-1-(isoquinolin-1-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-olHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 219489224-(5-Fluoro-2-hydroxyphenyl)-1-(isoquinoline-1-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-olYield 52.1%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Analogously to Example 2, 65 mg (0.15 mmol) of 4-(5-fluoro-2-methoxyphenyl)-1-(isoquinolin-1-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol is reacted with 2.7 ml of 1 M boron tribromide-CH2Cl2 solution. After chromatography on silica gel with hexane-ethyl acetate (0-80%), 33 mg of the product is obtained.

Sources & evidence

ORD record
ord-0c7f35fd182d4a31ac8cde07c19e5a7f
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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