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

HRID 2215423Notes

Reaction equation

HRID 2215423 reaction equation
[N:1]1[C:10]2[C:5](=[C:6]([NH:11][CH2:12][C:13]([C:28]([F:31])([F:30])[F:29])([OH:27])[CH2:14][C:15]3([C:18]4[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=4[O:25]C)[CH2:17][CH2:16]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br>ClCCl>[N:1]1[C:10]2[C:5](=[C:6]([NH:11][CH2:12][C:13]([C:28]([F:31])([F:29])[F:30])([OH:27])[CH2:14][C:15]3([C:18]4[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=4[OH:25])[CH2:17][CH2:16]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 219488751-(Quinolin-5-ylamino)-3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-(trifluoromethyl)propan-2-ol

Product 1

HCID 219488721-(Quinolin-5-ylamino)-3-[1-(5-fluoro-2-hydroxyphenyl)cycloprop-1-yl]-2-(trifluoromethyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Analogously to Example 38, 330 mg (0.76 mmol) of 1-(quinolin-5-ylamino)-3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-(trifluoromethyl)propan-2-ol is reacted with 3.80 ml (3.80 mmol) of a 1 M boron tribromide solution in 6.90 ml of dichloromethane. After 2 hours, the reaction is halted. The recrystallization from ethyl acetate and methanol yields 292 mg (91% of theory) of the product.

Workup

  1. customThe recrystallization from ethyl acetate and methanol
  2. customyields 292 mg (91% of theory) of the product

Sources & evidence

ORD record
ord-4a4af9f443794a339b38f31cfd045c4a
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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