Methanol → HCID 21948809, compound

HRID 2054983Notes

Reaction equation

HRID 2054983 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]([CH2:23][OH:24])=[N:18]3)[CH:7]=1.B(Br)(Br)Br.CO>ClCCl>[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]([CH2:23][OH:24])=[N:18]3)[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 21948888HCID 21948888, compound

Product 1

HCID 21948809HCID 21948809, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

290 mg (0.62 mmol) of 4-(5-fluoro-2-methoxyphenyl)-1-(2-(hydroxymethyl)quinolin-5-ylamino)-4-methyl-2-(trifluoromethyl)pentan-2-ol in 7.0 ml of dichloromethane is mixed at room temperature with 12.5 ml (12.5 mmol) of a 1 M boron tribromide solution. After 20 hours at room temperature, the reaction is brought to a halt by adding methanol. The solvent is removed in a vacuum, the residue is taken up in saturated sodium bicarbonate solution and ethyl acetate, extracted with ethyl acetate, and the combined organic phases are dried on sodium sulfate. After the solvent is removed and after purification on silica gel with hexane-ethyl acetate (0-70%) as well as with ethyl acetate-methanol (0-10%), 160 mg (51% of theory) of the product is obtained.

Workup

  1. customThe solvent is removed in a vacuum
  2. extractionethyl acetate, extracted with ethyl acetate
  3. customthe combined organic phases are dried on sodium sulfate
  4. customAfter the solvent is removed
  5. customafter purification on silica gel with hexane-ethyl acetate (0-70%) as well as with ethyl acetate-methanol (0-10%), 160 mg (51% of theory) of the product
  6. customis obtained

Sources & evidence

ORD record
ord-8906b2bf565e4b03a2d1d30dc8630a98
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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