반응 #1869175

반응 방정식

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

용매

THF

THF

반응 조건

후처리

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

실험 절차

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.

출처