Reaktion #2289934

Reaktionsgleichung

compound 22-3

ethyl trans-4-(4-((2-bromobenzyl)(2-(3,5-dichloropyridin-4-yl)-2-oxoethyl)carbamoyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)cyclohexanecarboxylate

DMA

→

compound 22-4

Ausbeute 29.0%

ethyl trans-4-(4-((2-cyanobenzyl)(2-(3,5-dichloropyridin-4-yl)-2-oxoethyl)carbamoyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)cyclohexanecarboxylate

Ausbeute 29.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas purged with argon for 10 min
2. 2
   TemperaturThe reaction mixture was cooled to room temperature
3. 3
   Sonstigequenched with water (10 mL)
4. 4
   Extraktionextracted with EtOAc (2×20 mL)
5. 5
   WaschenThe combined organic layers were washed with water (10 mL) and brine (10 mL)
6. 6
   Trocknendried over Na2SO4
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified by column chromatography (silica gel, 30% EtOAc/hexane)

Vorschrift

A mixture of compound 22-3 (100 mg, 0.14 mmol) and Zn(CN)2 (34 mg, 0.28 mmol) in DMA (8 mL) was purged with argon for 10 min. Pd(PPh3)4 (33.4 mg, 0.02 mmol) was added and the mixture was heated at 100° C. for 3 h. The reaction mixture was cooled to room temperature, quenched with water (10 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with water (10 mL) and brine (10 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 30% EtOAc/hexane) to provide compound 22-4 (27 mg, 29%) as an off-white solid.

Quelle