Methanol → HCID 44544213, compound

HRID 2387339Notes

Reaction equation

HRID 2387339 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([CH2:18][C:19]1[NH:31][C:22]2=[CH:23][N:24]=[C:25]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:26]=[C:21]2[CH:20]=1)([OH:17])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15]C)([CH3:7])[CH3:6].B(Br)(Br)Br.CO>ClCCl>[F:14][C:12]1[CH:11]=[CH:10][C:9]([OH:15])=[C:8]([C:5]([CH3:7])([CH3:6])[CH2:4][C:3]([OH:17])([CH2:18][C:19]2[NH:31][C:22]3=[CH:23][N:24]=[C:25]([S:27]([CH3:30])(=[O:28])=[O:29])[CH:26]=[C:21]3[CH:20]=2)[C:2]([F:32])([F:1])[F:33])[CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 58026153HCID 58026153, compound

Product 1

HCID 44544213HCID 44544213, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-2-(5-methanesulfonyl-1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)-4-methylpentan-2-ol (179 mg, 0.37 mmol) was dissolved in 10 mL of dichloromethane. 3.7 mL of a 1 M solution of boron tribromide (3.7 mmol) in dichloromethane were added. The resulting solution was stirred at normal room temperature overnight. After dropwise addition of MeOH (1 mL) at 0° C., the solvent was evaporated. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate (NaHCO3) solution. The organic phase was separated and the aqueous layer was extracted with four 10 mL portions of ethyl acetate. The combined organic phases were dried over magnesium sulfate. The solvent was removed. Flash chromatography of the residue yielded 4-fluoro-2-[4,4,4-trifluoro-3-hydroxy-3-(5-methanesulfonyl-1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)-1,1-dimethylbutyl]phenol as a white solid.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate (NaHCO3) solution
  4. customThe organic phase was separated
  5. extractionthe aqueous layer was extracted with four 10 mL portions of ethyl acetate
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-9fc6701fd18446369abc5a16753a22f3
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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