Reaction #1869175

Reaction equation

n-butyllithium

3-indolylacetic acid

(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl chloride

→

title compound

{1-[(6-Chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1H-indol-3-yl}acetic acid

Solvents

THF

THF

Conditions

Workup

1. 1
   Concentrationconcentrated in vacuo
2. 2
   workup.ADDITIONThe resultant residue is treated with 1 M aq HCl (˜2 mL) and water (3 mL)
3. 3
   Extractionextracted with dichloromethane
4. 4
   Dryingdried (MgSO4)
5. 5
   Concentrationconcentrated in vacuo
6. 6
   WashChromatography of this residue, eluting with ethyl acetate

Procedure

A stirred solution of 3-indolylacetic acid (175 mg, 1.00 mmol) in THF is cooled to −78° C. under nitrogen and treated portionwise with 2.5 M n-butyllithium in hexanes (0.84 mL, 2.10 mmol) over a 10 min. period. After 1 h at −78° C., the reaction mixture is treated with (6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl chloride (257 mg, 1.00 mmol) in THF, allowed to warm to ambient temperature, stirred for 24 h and concentrated in vacuo. The resultant residue is treated with 1 M aq HCl (˜2 mL) and water (3 mL) and extracted with dichloromethane. The extracts are combined, dried (MgSO4) and concentrated in vacuo. Chromatography of this residue, eluting with ethyl acetate, affords the title compound as a light tan solid, 32 mg, mp 220-222° C. (darkens>200° C.), identified by mass spectral and NMR analyses.

Source