Sodium Iodide → 3-(5-Chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid iodomethyl ester

HRID 585160Notes

Reaction equation

HRID 585160 reaction equation
Cl[CH2:2][O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=2)[C@@:8]([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=2[O:27][CH3:28])([F:19])[C:7]1=[O:29])=[O:5].[I-:30].[Na+]>CC(C)=O>[I:30][CH2:2][O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=2)[C:8]([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=2[O:27][CH3:28])([F:19])[C:7]1=[O:29])=[O:5]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86759802(S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid chloromethyl ester

Product 1

HCID 208227933-(5-Chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid iodomethyl esterYield 84.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 25 mL flask containing (S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid chloromethyl ester ((S)-XII) (0.633 g, 1.40 mmol) was added 6 mL anhydrous acetone, and sodium iodide (0.314 g, 2.10 mmol). The reaction was heated to reflux and stirred for 4 hours, then the reaction was cooled to room temperature, and the solvent was evaporated in vacuo. The crude oil was dissolved in dichloromethane and washed with a 1% aq. sodium thiosulfate solution. The organic layer was separated, dried (Na2SO4) and evaporated in vacuo producing the title compound (0.640 g, 84%) which was used in subsequent reactions without purification. 1H NMR (CDCl3 400 MHz): δ=8.38 (s, 1H), 7.78 (s, 1H), 7.48 (d, 1H, J=7 Hz), 7.36 (d, 1H, J=7 Hz), 7.31 (d, 1H, J=7 Hz), 6.77 (d, 1H, J=7 Hz), 6.28 (d, 1H, J=6.4 Hz), 6.18 (d, 1H, J=6.4 Hz), 3.56 (s, 3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customthe solvent was evaporated in vacuo
  4. dissolutionThe crude oil was dissolved in dichloromethane
  5. washwashed with a 1% aq. sodium thiosulfate solution
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-c510b44051c244d99a4878336b27139c
Source dataset
uspto-grants-2005_08
Patent number
US06930100B2

Reaction notes

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