反应详情

温度

90 °C

A mixture containing 4-amino-3-nitrophenol 5 (1.0 g, 6.4 mmol), potassium bis(trimethylsilyl)amide (2.58 g, 12.8mmol) was stirred in DMF (50 ml) for 2 hours at rt. To this mixture was added (4-chloro(2-pyridyl))-N-methylcarboxamide 4 (1.09 g, 6.4 mmol) and potassium carbonate (0.5 g, 7.6 mmol) and stirred at 90° C. overnight. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine (2×10 ml), dried, filtered and concentrated in vacuum to give brown solid. Purification on silica gel with 2% triethyl amine in 50% ethyl acetate in hexane gave 1.3 g (yield, 72%) of [4-(4-amino-3-nitrophenoxy)(2-pyridyl)]-N-methylcarboxamide 6 as an orange solid: 1H NMR (300 MHz, CDCl3) δ 8.40 (d, J=5.6 Hz, 1 H), 7.99 (br s, 1 H), 7.90 (d, J=2.7 Hz, 1 H), 7.64 (d, J=2.7 Hz, 1 H), 7.17 (dd, J=2.7, 9.0 Hz, 1 H), 6.95 (ddd, J=0.7, 2.5, 5.6 Hz, 1 H) 6.89 (d, J=9.0 Hz, 1 H), 6.18 (br s, 2 H), 3.00 (d, J=5.1 Hz, 3 H); mp 208–210° C. dec; LCMS m/z 289.2 (MH+), tR=1.92 min.

1. concentrationThe reaction mixture was then concentrated
2. custompartitioned between ethyl acetate and water
3. customThe organic layer was separated
4. washwashed with brine (2×10 ml)
5. customdried
6. filtrationfiltered
7. concentrationconcentrated in vacuum
8. customto give brown solid
9. customPurification on silica gel with 2% triethyl amine in 50% ethyl acetate in hexane