Sodium Hydroxide → HCID 22497255, compound

HRID 1816111Notes

Reaction equation

HRID 1816111 reaction equation
FC(F)(F)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([S:14][CH3:15])=[CH:11][CH:12]=2)[N:7]([CH:16]([CH3:18])[CH3:17])[CH:6]=1)=[O:4].[OH-:21].[Na+]>O1CCCC1>[CH:16]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([S:14][CH3:15])[CH:9]=2)[C:5]([C:3]([OH:4])=[O:21])=[CH:6]1)([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22497235HCID 22497235, compound

Product 1

HCID 22497255HCID 22497255, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2,2,2-trifluoro-1-(1-isopropyl-6-methylsulfanyl-1H-indol-3-yl)-ethanone (200 mg, 0.77 mmol) in tetrahydrofuran (1 mL) at 25° C. was treated with a 20% aqueous sodium hydroxide solution (2 mL). The mixture was heated at 100° C. for 24 h. At this time, the reaction was cooled to 25° C. and was partitioned between water (40 mL) and ethyl acetate (40 mL). The solution was treated with a 1N aqueous hydrochloric acid solution. The layers were then shaken and separated. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 2/1 hexanes/ethyl acetate) afforded 1-isopropyl-6-methylsulfanyl-1H-indole-3-carboxylic acid (126 mg, 77%) as a white solid: mp 132-133° C.; EI-HRMS m/e calcd for C13H15NO2S (M+) 249.0823, found 249.0819.

Workup

  1. temperatureAt this time, the reaction was cooled to 25° C.
  2. customwas partitioned between water (40 mL) and ethyl acetate (40 mL)
  3. additionThe solution was treated with a 1N aqueous hydrochloric acid solution
  4. customseparated
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-856577aaa437421c8bac39882cf483b6
Source dataset
uspto-grants-2005_04
Patent number
US06881844B2

Reaction notes

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