Boron tribromide → 3-[1-(5-Fluoro-2-hydroxyphenyl)cycloprop-1-yl]-1-(2-methylquinolin-5-ylamino)-2-(trifluoromethyl)propan-2-ol

HRID 2215426Notes

Reaction equation

HRID 2215426 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31]C)=[C:6]([C:8]2([CH2:11][C:12]([C:27]([F:30])([F:29])[F:28])([OH:26])[CH2:13][NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH:17]=[CH:18][C:19]([CH3:25])=[N:20]4)[CH2:10][CH2:9]2)[CH:7]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:31])=[C:6]([C:8]2([CH2:11][C:12]([C:27]([F:28])([F:29])[F:30])([OH:26])[CH2:13][NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH:17]=[CH:18][C:19]([CH3:25])=[N:20]4)[CH2:9][CH2:10]2)[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 219488813-[1-(5-Fluoro-2-methoxyphenyl)cycloprop-1-yl]-1-(2-methylquinolin-5-ylamino)-2-(trifluoromethyl)propan-2-ol

Product 1

HCID 219489123-[1-(5-Fluoro-2-hydroxyphenyl)cycloprop-1-yl]-1-(2-methylquinolin-5-ylamino)-2-(trifluoromethyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Analogously to Example 38, 395 mg (0.88 mmol) of 3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-1-(2-methylquinolin-5-ylamino)-2-(trifluoromethyl)propan-2-ol is reacted with 4.30 ml (4.3 mmol) of a 1 M boron tribromide solution in 8.0 ml of dichloromethane. After one hour at 0° C., the reaction is halted. The subsequent recrystallization from ethyl acetate, acetone and methanol yields 257 mg (67% of theory) of the product.

Workup

  1. customThe subsequent recrystallization from ethyl acetate, acetone and methanol
  2. customyields 257 mg (67% of theory) of the product

Sources & evidence

ORD record
ord-a7a3816b6b4744719a66bceb7b9fdf92
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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