Reaktion #597461

Reaktionsgleichung

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

1-methyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indazole

K2CO3

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

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 reaction mixture of (S)-2-(7-bromo-2-chloro-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (300 mg, 0.65 mmol), 1-methyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indazole (260 mg, 0.78 mmol), Pd(PPh3)4 (75 mg, 0.065 mmol), 2N K2CO3 (1.6 mL) in dioxane (5 mL) was heated at 95° C. for hours. After the reaction finished, 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 C33H36BrN3O3S: 634.2 (M+H+); Found: 634.1 (M+H+).

Quelle