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

HRID 2054921Notes

Reaction equation

HRID 2054921 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-3928581a0aa8400381cf850d48836364
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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