Methanol → HCID 86753138, compound

HRID 2394453Notes

Reaction equation

HRID 2394453 reaction equation
C(Cl)Cl.O[CH:5]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:6][N:7]1[C:15]2[C:10](=[C:11]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.C(N(S(F)(F)[F:36])CC)C.CO>O>[F:36][CH:5]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:6][N:7]1[C:15]2[C:10](=[C:11]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 123472(Diethylamino)sulfur trifluorideHCID 86753139HCID 86753139, compound

Product 1

HCID 86753138HCID 86753138, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-34 °C

Procedure

To 10 ml of methylene chloride, there was dissolved 134 mg of 5-[1-(2-hydroxy-2-phenylethyl)indol-4-yl]methyl-2,4-thiazolidinedione prepared in Example 323 under an argon gas atmosphere and the resulting solution was then cooled to -34° C. After addition of 88 mg of diethylaminosulfur trifluoride to the solution and stirring it for 5 minutes and the solution was then stirred at room temperature for additional 30 minutes. After addition of 10 ml of methanol, the solution was poured into 50 ml of water and extracted with ethyl acetate. The resulting extract was dried over anhydrous sodium sulfate and the solvent was removed through evaporation under reduced pressure to give a crude product. The product was purified by preparatory silica gel thin layer chromatography (hexane:ethyl acetate=10:1) to give 98 mg of 5-[1-(2-fluoro-2-phenylethyl)indol-4-yl]methyl-2,4-thiazolidinedione as a yellow amorphous substance. The yield thereof was found to be 73%.

Workup

  1. stirringthe solution was then stirred at room temperature for additional 30 minutes
  2. extractionextracted with ethyl acetate
  3. extractionThe resulting extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customthe solvent was removed through evaporation under reduced pressure
  6. customto give a crude product
  7. customThe product was purified by preparatory silica gel thin layer chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-ad57670925b84c9ca69b3b592c0e6cfc
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

Loading…