Reaktion #1127205

Reaktionsgleichung

product

(5-bromo-1,3-thiazol-2-yl)(dicyclopropyl)methanol

crude product

4-[3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine

Na2CO3

dichloromethane

→

dicyclopropyl{5-[3-(morpholin-4-yl)-5-nitrophenyl]-1,3-thiazol-2-yl}methanol

Ausbeute 68.2%

Lösungsmittel

DME

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered through a celite pad with dichloromethane
2. 2
   Einengenthe filtrate was concentrated
3. 3
   SonstigeThe residue was purified twice by chromatography on silica gel (0-100% ethyl acetate in hexanes

Vorschrift

A solution of the product of Step 2 (239 mg, 0.872 mmol), crude product of Step 3 (320 mg, ˜0.96 mmol), Pd(dppf)Cl2 (31.9 mg, 0.044 mmol) and Na2CO3 (aq) (2.0 M, 1.3 mL, 2.6 mmol) in DME (4.4 mL) was irradiated to 130° C. in the microwave for 35 minutes. The reaction mixture was filtered through a celite pad with dichloromethane and the filtrate was concentrated. The residue was purified twice by chromatography on silica gel (0-100% ethyl acetate in hexanes then 0-60% dichloromethane in ethyl acetate) to give the desired dicyclopropyl{5-[3-(morpholin-4-yl)-5-nitrophenyl]-1,3-thiazol-2-yl}methanol (239 mg, 0.595 mmol, 68% yield) as a yellow solid. MS APCI: [M-OH]+ m/z 385.1.

Quelle