1-(2,3-Dihydro-1H-indol-1-yl)ethan-1-one → 1-Acetyl-6-trifluoromethyl-5-trifluoromethylsulphonyloxy-indoline

HRID 427732Notes

Reaction equation

HRID 427732 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[F:13][C:14]([F:27])([F:26])[S:15]([O:18]S(C(F)(F)F)(=O)=O)(=[O:17])=[O:16]>N1C=CC=CC=1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:18][S:15]([C:14]([F:27])([F:13])[F:26])(=[O:16])=[O:17])=[C:10]([C:14]([F:27])([F:26])[F:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 276731-(2,3-Dihydro-1H-indol-1-yl)ethan-1-oneHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 105716161-Acetyl-6-trifluoromethyl-5-trifluoromethylsulphonyloxy-indolineYield 173.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the acetylindoline (D11, 1.19 g, 4.9 mmol) in dry pyridine (10 ml) at 0° C. was added trifluoromethanesulphonic anhydride (1.52 g, 5.4 mmol). The mixture was then stirred overnight, while slowly warming to room temperature. The mixture was partially evaporated, the residual liquor was diluted well with water and the precipitate was filtered off. The crude product was dissolved in dichloromethane and the solution was washed with IN hydrochloric acid and brine, dried and evaporated to give the title compound (1.77 g, 96%).

Workup

  1. customThe mixture was partially evaporated
  2. additionthe residual liquor was diluted well with water
  3. filtrationthe precipitate was filtered off
  4. dissolutionThe crude product was dissolved in dichloromethane
  5. washthe solution was washed with IN hydrochloric acid and brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-eea64a5abc8843b2afff9060b0a1e2e4
Source dataset
uspto-grants-2001_11
Patent number
US06313145B1

Reaction notes

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