Sodium Bicarbonate → 4-(5-Fluoro-2-hydroxyphenyl)-1-(2-methoxyquinolin-5-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol

HRID 2054939Notes

Reaction equation

HRID 2054939 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:32]C)=[C:6]([C:8]([CH3:31])([CH3:30])[CH2:9][C:10]([C:26]([F:29])([F:28])[F:27])([OH:25])[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]([O:23][CH3:24])=[N:18]3)[CH:7]=1.B(Br)(Br)Br.C(Cl)Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:32])=[C:6]([C:8]([CH3:30])([CH3:31])[CH2:9][C:10]([C:26]([F:27])([F:28])[F:29])([OH:25])[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]([O:23][CH3:24])=[N:18]3)[CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 219488414-(5-Fluoro-2-methoxyphenyl)-1-(2-methoxyquinolin-5-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-olHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 219489234-(5-Fluoro-2-hydroxyphenyl)-1-(2-methoxyquinolin-5-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-olYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.21 mmol) of 4-(5-fluoro-2-methoxyphenyl)-1-(2-methoxyquinolin-5-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol in 9 ml of CH2Cl2 is mixed at room temperature with 4 ml of 1M boron tribromide-CH2Cl2 solution. After 15 hours at room temperature, the batch is poured into saturated NaHCO3 solution, stirred for 10 minutes and extracted with ethyl acetate. The combined organic extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. Chromatography on silica gel with hexane/ethyl acetate yields 73 mg of the product.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts are dried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-ec3bf390c4fa4a4ba1a5655d16ee2950
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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