Water → 2-Fluoro-4-(1-isopropyl-6-methanesulfonylamino-1H-indol-3-yl)-thiobenzamide

HRID 2079901Notes

Reaction equation

HRID 2079901 reaction equation
C(N(C(C)C)CC)(C)C.O.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:27]3[C:22](=[CH:23][C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:26]=3)[N:21]([CH:33]([CH3:35])[CH3:34])[CH:20]=2)=[CH:15][C:14]=1[F:36])#[N:12].C(OP(=S)(OCC)[SH:41])C>COOOC>[F:36][C:14]1[CH:15]=[C:16]([C:19]2[C:27]3[C:22](=[CH:23][C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:26]=3)[N:21]([CH:33]([CH3:34])[CH3:35])[CH:20]=2)[CH:17]=[CH:18][C:13]=1[C:11]([NH2:12])=[S:41]

Participants

6

Reactant 4

HCID 962WaterHCID 9274O,O-Diethyl dithiophosphateHCID 81531DiisopropylethylamineHCID 51346768N-(3-(4-cyano-3-fluorophenyl)-1-isopropyl-1H-indol-6-yl)methanesulfonamide

Product 1

HCID 574422582-Fluoro-4-(1-isopropyl-6-methanesulfonylamino-1H-indol-3-yl)-thiobenzamideYield 91%

Reagents, catalysts & solvents 1

HCID 17819761Trioxide, dimethylSolvent

Procedure

Add a drop of di-isopropylethylamine and a drop of water to N-[3-(4-Cyano-3-fluoro-phenyl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide (100 mg, 0.27 mmol) in 10 mL of dimethoxy ether. Heat to reflux, followed by addition of dithiophosphoric acid O,O′-diethyl ester (151 mg, 0.81 mmol), and reflux in a sealed tube overnight. Evaporate the solvent. Purification of the residue using silica gel chromatography eluted with EtOAc and hexane gradient to give 99 mg (91%) of the desired product.

Workup

  1. temperatureHeat
  2. temperatureto reflux
  3. temperaturereflux in a sealed tube overnight
  4. customEvaporate the solvent
  5. customPurification of the residue
  6. washeluted with EtOAc and hexane gradient

Sources & evidence

ORD record
ord-300c318fdc504cbbb05bffd73a528c85
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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