反应详情

温度

85 °C

To carbonic acid 3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl ester methyl ester (0.2 g, 0.62 mmol), 1-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-piperazine (0.2 g, 0.68 mmol), bis-diphenylphosphinopentane (0.08 g, 0.18 mmol), potassium carbonate (0.26 g, 1.85 mmol) and allyl palladium (II) chloride dimer (0.034 g, 0.09 mmol) was added dimethyl formamide (6 mL). The reaction was degassed with an argon stream for 10 min. The reaction was stirred at 85° C. for 18 h. The reaction was cooled to room temperature, poured onto crushed ice-water (150 mL), filtered, washed with water, dried over sodium sulfate, filtered, and the solvent removed under vacuum. The residue was purified by silica gel column chromatography using 10% methanol in dichloromethane to afford P-423 (0.05 g, 18% yield) as light brown gummy solid. 1H NMR (400 MHz, DMSO-d6): 3.20 (br s, 3H) 3.55-3.99 (m, 10H), 6.95 (d, J=8.59 Hz, 1H), 7.11 (br s, 1H), 7.23-7.39 (m, 3H), 7.39-7.55 (m, 2H), 7.69 (br s, 1H), 8.02 (s, 1H), 9.33 (br s, 2H) ppm. Calc. 411.9; APCI+ (M+1): 412.1, 97%.

1. customThe reaction was degassed with an argon stream for 10 min
2. temperatureThe reaction was cooled to room temperature
3. additionpoured
4. customonto crushed ice-water (150 mL)
5. filtrationfiltered
6. washwashed with water
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customthe solvent removed under vacuum
10. customThe residue was purified by silica gel column chromatography
11. customto afford P-423 (0.05 g, 18% yield) as light brown gummy solid