Reaktion #597462

Reaktionsgleichung

EtOAc

(S)-2-(7-bromo-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)phenyl)benzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

4-chlorophenylboronic acid

NaHCO3

→

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)phenyl)benzo[d]thiazol-6-yl)ethyl pivalate

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed 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
7. 7
   Wascheneluting by 0-100% EtOAc in hexanes
8. 8
   Sonstigeto give the product

Vorschrift

The mixture of (S)-2-(7-bromo-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)phenyl)benzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (24 mg, 0.0379 mmol), 4-chlorophenylboronic acid (9 mg, 0.0568 mmol), 2N NaHCO3 (100 μL), Pd(PPh3)4 (4 mg, 0.0038 mmol) in dioxane (2 mL) was heated at 120° C. for 3 hrs. The reaction mixture was diluted by EtOAc, washed by sat. NaHCO3, extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C39H40ClN3O3S: 666.2 (M+H+); Found: 666.1 (M+H+).

Quelle