Reaction #72580

Reaction equation

compound

6-Fluoro-5-(hydroxymethyl)-3-{[4-(4-morpholinylmethyl)-1H-pyrrol-2-yl]methylene}-1,3-dihydro-2H-indol-2-one

thiazolidine-2,4-dione

triphenylphosphine

tert-butyl azodicarboxylate

Thiazolidine-2,4-dione

triphenylphosphine

di-tert-butyl azodicarboxylate

→

title product

3-[(6-Fluoro-3-{[4-(4-morpholinylmethyl)-1H-pyrrol-2-yl]methylene}-2-oxo-2,3-dihydro-1H-indol-5-yl)methyl]-1,3-thiazolidine-2,4-dione

Solvents

THF

CH3CN

Conditions

Workup

1. 1
   TemperatureThe mixture is cooled in an ice bath
2. 2
   workup.STIRRINGThe mixture is stirred at 0° C. for 1.5 hours
3. 3
   workup.ADDITIONSilica gel is added
4. 4
   Otherthe mixture is evaporated in vacuo
5. 5
   OtherThe residue obtained
6. 6
   Otheris purified by flash chromatography (DCM/MeOH 100:0 to 95:5)
7. 7
   Otherto yield a dark yellow solid which

Procedure

Thiazolidine-2,4-dione (0.350 mmol) and triphenylphosphine on resin (1.66 mmol/g, 0.415 mmol) are stirred for 10 min. at ambient temperature in anhydrous THF (9 ml) under nitrogen. The mixture is cooled in an ice bath and di-tert-butyl azodicarboxylate (0.369 mmol) is added all at once. The mixture is stirred at 0° C. for 10 min, and then the compound obtained in Step D (0.238 mmol) is added all at once. The mixture is stirred at 0° C. for 1.5 hours, and then thiazolidine-2,4-dione (0.350 mmol), three portions of triphenylphosphine on resin (1.66 mmol/g; 0.166 mmol, 0.415 mmol and 0.166 mmol) and three portions of tert-butyl azodicarboxylate (each portion 0.369 mmol) are added over a period of 48 hours. Silica gel is added and the mixture is evaporated in vacuo. The residue obtained is purified by flash chromatography (DCM/MeOH 100:0 to 95:5) to yield a dark yellow solid which, after trituration in CH3CN, yields the title product in the form of a yellow solid.

Source