2-(1-Benzenesulfonyl-5-bromo-1H-indol-2-ylmethyl)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-ol → 2-(5-Bromo-1H-indol-2-ylmethyl)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-ol

HRID 400683Notes

Reaction equation

HRID 400683 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([Br:19])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:20][C:21]([OH:40])([CH2:26][C:27]([C:30]2[C:38]3[O:37][CH2:36][CH2:35][C:34]=3[CH:33]=[C:32]([Cl:39])[CH:31]=2)([CH3:29])[CH3:28])[C:22]([F:25])([F:24])[F:23])(=O)=O)C=CC=CC=1>CO.[OH-].[Na+].[Cl-].[Na+].O>[Br:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][C:11]([CH2:20][C:21]([OH:40])([CH2:26][C:27]([C:30]1[C:38]3[O:37][CH2:36][CH2:35][C:34]=3[CH:33]=[C:32]([Cl:39])[CH:31]=1)([CH3:29])[CH3:28])[C:22]([F:25])([F:23])[F:24])=[CH:12]2

Participants

5

Reactant 1

HCID 600264582-(1-Benzenesulfonyl-5-bromo-1H-indol-2-ylmethyl)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-ol

Product 1

HCID 600265542-(5-Bromo-1H-indol-2-ylmethyl)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-olYield 63.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2-(1-benzenesulfonyl-5-bromo-1H-indol-2-ylmethyl)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-ol (30 mg, 0.046 mmol) in 5 mL of methanol and 5 mL of 10% aqueous sodium hydroxide solution was warmed at reflux. After 18 hours, the mixture was diluted with brine and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with three 5 mL portions of brine, three 5 mL portions of saturated aqueous ammonium chloride solution, 5 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by preparative TLC (1 mm, silica gel, ethyl acetate-hexanes (3:7)) to afford 15 mg (63% yield) of the title compound.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux
  3. extractionextracted with three 7 mL portions of ethyl acetate
  4. washThe combined organic layers were washed with three 5 mL portions of brine, three 5 mL portions of saturated aqueous ammonium chloride solution, 5 mL of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by preparative TLC (1 mm, silica gel, ethyl acetate-hexanes (3:7))

Sources & evidence

ORD record
ord-6252bad7f35d4df3b04f2f938f80fd79
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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