反应详情

温度

130 °C

A 5 mL sealable heavy walled glass tube suitable for microwave heating was charged with 213 mg (1.00 mmol) of 4,6-diamino-2-bromo-nicotinonitrile, 183 mg (1.5 mmol) of phenylboronic acid, 11 mg (0.050 mmol) of palladium(II)acetate, 60 mg (0.020 mmol) of tri(o-tolyl)phosphine, and 220 mg (2.05 mmol) of sodium carbonate. To this mixture was added 2 mL of DMF, 2 mL of THF, and 1 mL of water. The tube was sealed, then heated with a microwave apparatus at 130° C. for 20 min. The mixture was poured into 20 mL of water, extracted with ethyl acetate (3×10 mL). The combined ethyl acetate layers were back extracted with 1M NaOH(aq.) (2×10 mL) and brine (1×10 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The product was partially purified via silica gel chromatography, eluting with 60:40 ethyl acetate:hexanes to provide an off-white solid. This was taken up in ethyl acetate, then hexane was added (until about 50:50 hexanes:ethyl acetate) to precipitate 63 mg (30%) of white crystals. 1H NMR (300 MHz, d6-DMSO) δ 7.66 (m, 2H), 7.45 (m, 3H), 6.35 (s, 2H), 6.25 (s, 2H), 5.69 (s, 1H); MS (ESI) m/e 211 (M+H)+, 209 (M−H)−.

1. temperatureA 5 mL sealable heavy walled glass tube suitable for microwave heating
2. customThe tube was sealed
3. extractionextracted with ethyl acetate (3×10 mL)
4. extractionThe combined ethyl acetate layers were back extracted with 1M NaOH(aq.) (2×10 mL) and brine (1×10 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe product was partially purified via silica gel chromatography
9. washeluting with 60:40 ethyl acetate
10. customhexanes to provide an off-white solid
11. customto precipitate 63 mg (30%) of white crystals