Water → 7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-phenyl-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

3-bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (0.100 g, 0.210 mmol, Example 19), phenylboronic acid (0.0384 g, 0.315 mmol), bis(triphenylphosphine)palladium(II)chloride (0.0147 g, 0.021 mmol) and 1,2-dimethoxyethane (DME) (5 mL) were heated at 100° C. for 4 h in a 1,2-dimethoxyethane (DME) (5 mL)/water (5.00 mL) mixture. The reaction mixture was diluted with ethyl acetate (50 ml) and extracted with ethyl acetate (2×50 ml). The combined extracts were washed with brine and dried through a hydromatrix cartridge (Varian, 10 g). The filtrate was concentrated to an oil that was purified by mass-directed automated preparative HPLC to afford, after trituration in iso-hexane, 7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-phenyl-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (0.051 g, 0.108 mmol, 51.3% yield).

1. extractionextracted with ethyl acetate (2×50 ml)
2. washThe combined extracts were washed with brine
3. customdried through a hydromatrix cartridge (Varian, 10 g)
4. concentrationThe filtrate was concentrated to an oil that
5. customwas purified
6. customto afford

ORDレコード

ord-5bcbbc87aed24c2faeec9d64f745f212

出典データセット

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08513248B2