Reaktion #617971

Reaktionsgleichung

4-bromo-2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyridazin-3(2H)-one

tert-butyl (5-methyl-1,3,4-thiadiazol-2-yl)methylcarbamate

BINAP

Cs2CO3

→

title compound

tert-butyl (5-methyl-1,3,4-thiadiazol-2-yl)methyl(2-methyl-6-(((1S,2S)-2-(5-methyl pyridin-2-yl)cyclopropyl)methoxy)-3-oxo-2,3-dihydropyridazin-4-yl)carbamate

Lösungsmittel

EtOAc

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooled to rt
2. 2
   Waschenwashed with H2O and brine
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was purified by column chromatography on silica gel
7. 7
   Wascheneluting with PE/EA (1/2)

Vorschrift

A mixture of 4-bromo-2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyridazin-3(2H)-one (5) (90 mg, 0.26 mmol), tert-butyl (5-methyl-1,3,4-thiadiazol-2-yl)methylcarbamate (6) (119 mg, 0.52 mmol), Pd(OAc)2 (9 mg, 0.052 mmol), BINAP (36 mg, 0.057 mmol) and Cs2CO3 (127 mg, 0.39 mmol) in toluene (4 mL) under N2 was heated at 85° C. for 20 h. After cooled to rt, The mixture was diluted with EtOAc (20 mL), washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with PE/EA (1/2) to give the title compound as a oil.

Quelle