Cesium carbonate → HCID 59233383, compound

Temperature

110 °C

To a stirred solution of 3-bromo-4-methoxy-6-trifluoromethyl-pyridazine (D6) (0.79 g, 3.07 mmol), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (0.74 g, 3.69 mmol) and cesium carbonate (2.0 g, 6.14 mmol) in toluene (15 ml) in a sealed tube under nitrogen, were added (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.29 g, 0.46 mmol) and palladium(II) acetate (0.034 g, 0.15 mmol). The reactiom mixture was stirred at 110° C. for 18 h. After cooling to room temperature, the reaction mixture was filtered though Celite and the filtrate was evaporated. The crude product was purified by flash column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. to yield D7 (0.73 g, 63%) as a yellow solid. C16H23F3N4O3 requires 376; Found 377 (MH+).

1. temperatureAfter cooling to room temperature
2. filtrationthe reaction mixture was filtered though Celite
3. customthe filtrate was evaporated
4. customThe crude product was purified by flash column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane)
5. customThe desired fractions were collected
6. customevaporated in vacuo

ORD record

ord-7df0ef6da96c4be39665fc50b5f4f2ba

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906921B2