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

HRID 2182716Notes

Reaction equation

HRID 2182716 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:32]C)=[C:6]([C:8]2([CH2:11][C:12]([C:28]([F:31])([F:30])[F:29])([OH:27])[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]([CH2:25][OH:26])=[N:20]4)[CH2:10][CH2:9]2)[CH:7]=1.B(Br)(Br)Br>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:32])=[C:6]([C:8]2([CH2:11][C:12]([C:28]([F:29])([F:30])[F:31])([OH:27])[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]([CH2:25][OH:26])=[N:20]4)[CH2:10][CH2:9]2)[CH:7]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 219488603-[1-(5-Fluoro-2-methoxyphenyl)cycloprop-1-yl]-1-(2-(hydroxymethyl)quinolin-5-ylamino)-2-(trifluoromethyl)propan-2-ol

Product 1

HCID 219488503-[1-(5-Fluoro-2-hydroxyphenyl)cycloprop-1-yl]-1-(2-(hydroxymethyl)quinolin-5-ylamino)-2-(trifluoromethyl)propan-2-ol

Procedure

Analogously to Example 38, 100 mg (0.22 mmol) of 3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-1-(2-(hydroxymethyl)quinolin-5-ylamino)-2-(trifluoromethyl)propan-2-ol is reacted with 4.40 ml (4.40 mmol) of a 1 M boron tribromide solution. After working-up and purification on silica gel with hexane-ethyl acetate (0-100%) as well as with ethyl acetate-methanol (0-20%), 50 mg (50% of theory) of the product is obtained.

Workup

  1. custompurification on silica gel with hexane-ethyl acetate (0-100%) as well as with ethyl acetate-methanol (0-20%), 50 mg (50% of theory) of the product
  2. customis obtained

Sources & evidence

ORD record
ord-7025b866dd9843d9ad88ba474e97b681
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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