HCID 69760821, compound → HCID 60026668, compound

HRID 400671Notes

Reaction equation

HRID 400671 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:25][C:26]([OH:45])([CH2:31][C:32]([C:35]2[C:43]3[O:42][CH2:41][CH2:40][C:39]=3[CH:38]=[C:37]([Cl:44])[CH:36]=2)([CH3:34])[CH3:33])[C:27]([F:30])([F:29])[F:28])(=O)=O)C=CC=CC=1>CO.[OH-].[Na+].[Cl-].[Na+].O>[Cl:44][C:37]1[CH:36]=[C:35]([C:32]([CH3:34])([CH3:33])[CH2:31][C:26]([CH2:25][C:11]2[NH:10][C:18]3[C:13]([CH:12]=2)=[CH:14][C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:16][CH:17]=3)([OH:45])[C:27]([F:29])([F:28])[F:30])[C:43]2[O:42][CH2:41][CH2:40][C:39]=2[CH:38]=1

Participants

5

Reactant 1

HCID 69760821HCID 69760821, compound

Product 1

HCID 60026668HCID 60026668, compoundYield 42.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of the above 2-(1-benzenesulfonyl-5-pyridin-2-yl-1H-indol-2-ylmethyl)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-ol (30.1 mg, 0.046 mmol, theoretical maximum from above) in 5 mL of methanol and 5 mL of 10% aqueous sodium hydroxide solution was warmed at reflux. After 4 hours, the mixture was diluted with 7 mL of brine and extracted with three 5 mL portions of ethyl acetate. The combined organic layers were washed with three 5 mL portions of saturated aqueous sodium bicarbonate solution, 5 mL of brine, two 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 silica gel preparative TLC using ethyl acetate-hexanes (1:1). The material from the preparative TLC plate when concentrated in vacuo from diethyl ether-hexanes afforded 10 mg (42% yield) of the title compound.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux
  3. extractionextracted with three 5 mL portions of ethyl acetate
  4. washThe combined organic layers were washed with three 5 mL portions of saturated aqueous sodium bicarbonate solution, 5 mL of brine, two 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 silica gel preparative TLC
  9. concentrationThe material from the preparative TLC plate when concentrated in vacuo from diethyl ether-hexanes

Sources & evidence

ORD record
ord-d24e41e229254540a7903add183de597
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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