Potassium Acetate → tert-butyl 5-(3-(4-(methoxycarbonyl)phenoxy)pyrazin-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate

温度

80 °C

To a mixture of (amphos)2PdCl2 (0.145 g, 0.205 mmol), potassium acetate (1.045 g, 10.65 mmol), methyl 4-(3-chloropyrazin-2-yloxy)benzoate (1.084 g, 4.10 mmol), and tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate (1.900 g, 6.14 mmol) under N2 was added MeCN (7.0 mL) and Ar degassed water (0.70 mL). The reaction mixture was degassed with Ar (10 min) then heated to 80° C. for 20 h. The reaction mixture was diluted with H2O (20 mL) and extracted with EtOAc (2×10 mL). The combined organic extracts were washed with brine (10 mL), dried (MgSO4), and concentrated. Purification by ISCO (120 g SiO2, 10-100% EtOAc/hexanes) gave tert-butyl 5-(3-(4-(methoxycarbonyl)phenoxy)pyrazin-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate as a yellow oil.

1. customdegassed water (0.70 mL)
2. customThe reaction mixture was degassed with Ar (10 min)
3. additionThe reaction mixture was diluted with H2O (20 mL)
4. extractionextracted with EtOAc (2×10 mL)
5. washThe combined organic extracts were washed with brine (10 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. customPurification by ISCO (120 g SiO2, 10-100% EtOAc/hexanes)

ORDレコード

ord-8574714a701c4212a0b2ad43fc82b546

出典データセット

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08329700B2