Reaktion #597453

Reaktionsgleichung

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

3-bromophenylboronic acid

MeOH

NaOH

→

product

Ausbeute 36.0%

(S)-2-(2-(3-bromophenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol

Ausbeute 36.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThen the reaction was cooled down and to the mixture
2. 2
   Temperaturheated at 45° C
3. 3
   Waschenthe reaction was washed by water
4. 4
   Extraktionextracted by EtOAc
5. 5
   TrocknenThe organic phase was dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated down
8. 8
   Sonstigepurified by silica gel column
9. 9
   Wascheneluting by 0-50% EtOAc in hexanes

Vorschrift

To a solution of (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (310 mg, 0.577 mmol) in dioxane (5 mL), was added 3-bromophenylboronic acid (173 mg, 0.865 mmol), Ph(PPh3)4 (33 mg, 0.029 mmol) 2N K2CO3 (850 μL) in sealed tube. The reaction mixture was heated at 90° C. for 3 hs. Then the reaction was cooled down and to the mixture was added MeOH (5 mL), 2N NaOH (1.5 mL) and heated at 45° C. After the reaction was finished, the reaction was washed by water, extracted by EtOAc. The organic phase was dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-50% EtOAc in hexanes to give the product (110 mg, 36%). LCMS-ESI+: calc'd for C26H25BrClNO2S: 530.0 (M+H+); Found: 530.2 (M+H+).

Quelle