Cesium carbonate → (R)-t-butyl 4-(3-(1-(2,4-dichlorophenyl)ethylamino)-4-fluorophenyl)piperazine-1-carboxylate

温度

100 °C

To a mixture of t-butyl 4-(4-fluoro-3-(trifluoromethylsulfonyloxy)phenyl)piperazine-1-carboxylate (0.50 g, 1.17 mmol) and (IR)-1-(2,4-dichlorophenyl)ethanamine (0.58 g, 3.05 mmol), tBuDavePhos (0.025 g, 0.070 mmol), and Cs2CO3 (0.80 g, 2.44 mmol) in triethylamine (3 mL) was purged with nitrogen for 3 min. Addition of Pd2(dba)3 (0.034 g, 0.037 mmol) was followed, and the mixture was purged with nitrogen for 1 min. The resulting mixture was heated at 100° C. under nitrogen for 4 h. After cooling to room temperature, the suspension was filtered through a plug of Celite, and washed with ethyl acetate (25 mL). The filtrate was concentrated in vacuo and the resulting residue purified by flash chromatography (SiO2, 10-50% ethyl acetate in hexanes) to afford (R)-t-butyl 4-(3-(1-(2,4-dichlorophenyl)ethylamino)-4-fluorophenyl)piperazine-1-carboxylate (0.36 g, 42.9 mmol, 62%).

1. customwas purged with nitrogen for 3 min
2. customthe mixture was purged with nitrogen for 1 min
3. temperatureAfter cooling to room temperature
4. filtrationthe suspension was filtered through a plug of Celite
5. washwashed with ethyl acetate (25 mL)
6. concentrationThe filtrate was concentrated in vacuo
7. customthe resulting residue purified by flash chromatography (SiO2, 10-50% ethyl acetate in hexanes)

ORDレコード

ord-3c8d9d63d14046f789c0cf16292fed82

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08835419B2