Reaktion #597446

Reaktionsgleichung

(S)-2-(2-(3-(benzyloxy)phenyl)-7-bromo-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

4-chlorophenylboronic acid

K2CO3

→

product

Ausbeute 97.8%

(S)-2-(2-(3-(benzyloxy)phenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

Ausbeute 97.8%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe reaction mixture was washed by sat. NaHCO3
2. 2
   Extraktionextracted by EtOAc
3. 3
   Trocknenthe organic phase was dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated down
6. 6
   Sonstigepurified by silica gel column (0-50% EtOAc in Hexanes)

Vorschrift

The mixture of (S)-2-(2-(3-(benzyloxy)phenyl)-7-bromo-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (100 mg, 0.164 mmol), 4-chlorophenylboronic acid (38 mg, 0.246 mmol), 2N K2CO3 (400 μL), Pd(PPh3)4 (18 mg, 0.016 mmol) in dioxane in sealed tube was heated at 120° C. After the reaction is finished, the reaction mixture was washed by sat. NaHCO3, extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated down and purified by silica gel column (0-50% EtOAc in Hexanes) to give the product (103 mg, 97%). LCMS-ESI+: calc'd for C38H40ClNO4S: 642.2 (M+H+); Found: 642.3 (M+H+).

Quelle