Isopropyl iodide → HCID 22497235, compound

HRID 1816110Notes

Reaction equation

HRID 1816110 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([S:14][CH3:15])=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].I[CH:25]([CH3:27])[CH3:26]>CN(C)C=O>[F:17][C:2]([F:1])([F:16])[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:25]([CH3:27])[CH3:26])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 22497216HCID 22497216, compound

Product 1

HCID 22497235HCID 22497235, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2,2,2-trifluoro-1-(6-methylsulfanyl-1H-indol-3-yl)-ethanone (200 mg, 0.77 mmol) in N,N-dimethylformamide (2 mL) at 25° C. was treated with potassium carbonate (160 mg, 1.16 mmol). The reaction was stirred at 25° C. for 15 min and then was treated with 2-iodopropane (0.11 mL, 1.16 mmol). The reaction was stirred at 25° C. for 18 h and then was heated at 60° C. for 2 h. At this time, the reaction was cooled to 25° C. and was partitioned between water (50 mL) and ethyl acetate (50 mL). The layers were separated. The aqueous layer was extracted with ethyl acetate (1×50 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 3/1 hexanes/ethyl acetate) afforded 2,2,2-trifluoro-1-(1-isopropyl-6-methylsulfanyl-1H-indol-3-yl)-ethanone (216 mg, 93%) as an off-white solid: mp 67-69° C.; (ES)+-HRMS m/e calcd for C14H14F3NOS (M+) 301.0748, found 301.0740.

Workup

  1. stirringThe reaction was stirred at 25° C. for 18 h
  2. temperaturewas heated at 60° C. for 2 h
  3. temperatureAt this time, the reaction was cooled to 25° C.
  4. customwas partitioned between water (50 mL) and ethyl acetate (50 mL)
  5. customThe layers were separated
  6. extractionThe aqueous layer was extracted with ethyl acetate (1×50 mL)
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e9fa7aa5a904cbba326fd1e4284c8e7
Source dataset
uspto-grants-2005_04
Patent number
US06881844B2

Reaction notes

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