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With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; at 95℃;Inert atmosphere;
A mixture of tert-butyl 4-(2-chloropyrimidin-4-yl)piperazine-1-carboxylate (10.0g, 33.5mmol), (3,4-difluorophenyl)boronic acid (7.90 g, 50.2 mmol), 1M aq Na2CO3 (45 mL, 90.0 mmol), tetrakis(triphenylphosphine)palladium (0) (4.6 g, 4.02 mmol), and DME (300 mL) was stirred at 95 C overnight under N2 atmosphere. After cooling to room temperature, the mixture was stirred at room temperature for 15h, diluted with water, and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, and concentrated in vacuo to give 14 as a brown oil. This product was used for next reaction without further purification.
3-bromo-1-(3,5-difluorophenyl)-1,2,4-triazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50%
With pyridine; copper diacetate; In dichloromethane; at 20℃; for 72h;Molecular sieve;
Method 1: Diacetoxycopper (2.30 g, 12.7 mmol), 3,5-difluorophenyl-boronic acid (1.60 g, 10.1 mmol), <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (1.25 g, 8.4 mmol) and 4A molecular sieve (150mg) were mixed in DCM (50 mL), and pyridine (1.3 mL, 16.90 mmol) was added. The mixture was stined at RT under air for 3 days. LCMS showed that no starting material remained and desired product was formed. The reaction was filtered through a plug of Celite via suction and the solid was washed with additional DCM (200m1). The combined organic layer was washed with 0.1 N aqueous HC1 three times (50 ml x 3) and brine (200 ml). The organic layer was concentrated and purified on silica gel (120 g column, dry loading method on Celite) using 10-90percent EtOAc:Hexanes to afford 1.23 g (50percent) of desired product JW-lc. ?H NMR (400 MHz, DMSO-d6) oe 9.40 (s, 1H), 7.78 - 7.61 (m, 2H), 7.41 (tt, J = 9.3, 2.3 Hz, 1H) ppm. ESI-MS m/z calc. 258.95566, found 260.05 (M+1)+; Retention time: 0.8 minutes.
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