Sodium Bicarbonate → 1-(Quinolin-8-ylamino)-4-(5-fluoro-2-hydroxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-ol

HRID 2215371Notes

Reaction equation

HRID 2215371 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][CH2:12][C:13]([C:28]([F:31])([F:30])[F:29])([OH:27])[CH2:14][C:15]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[O:25]C)([CH3:17])[CH3:16])[CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.C(Cl)Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][CH2:12][C:13]([C:28]([F:31])([F:29])[F:30])([OH:27])[CH2:14][C:15]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[OH:25])([CH3:17])[CH3:16])[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 219488611-(Quinolin-8-ylamino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-olHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 219489211-(Quinolin-8-ylamino)-4-(5-fluoro-2-hydroxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-olYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg (0.46 mmol) of 1-(quinolin-8-ylamino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-ol in 20 ml of CH2Cl2 is mixed at 0° C. with 9 ml of 1 M boron tribromide-CH2Cl2 solution. After 20 hours at room temperature, the batch is poured into saturated NaHCO3 solution, stirred for 20 minutes and extracted with CH2Cl2. The combined organic extracts are washed with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Chromatography with hexane-ethyl acetate (0–25%) on silica gel yields 190 mg of the product.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic extracts are washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-e2b2ec7ddcc94903b720642a219eb895
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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