Реакция #45402

Уравнение реакции

mixture

3-bromo-7-iodothieno[3,2-c]pyridin-4-amine

(2-propynyloxy)benzene

PPh3

Et3N

DME water ethanol

→

desired product

Выход 27.0%

(2E)-3-[4-amino-3-(3-phenoxy-1-propynyl)thieno[3,2-c]pyridin-7-yl]-N-methylacrylamide

Выход 27.0%

Условия реакции

Обработка

1. 1
   КонцентрированиеThe reaction mixture was concentrated
2. 2
   Другоеthe residue was purified by HPLC

Методика

A mixture of Example 21A (150 mg, 0.48 mmol), (2-propynyloxy)benzene (0.13 mL, 0.96 mmol), PdCl2(PPh3)2 (17 mg, 0.024 mmol), PPh3 (15 mg, 0.057 mmol), CuI (3 mg), and Et3N (1 mL, 7.2 mmol) in DME/water/ethanol (70:30:20 mixture, 2 mL) was heated in a sealed vial to 125° C. for 25 minutes with stirring in a Smith Synthesizer microwave oven (at 300 W). The reaction mixture was concentrated and the residue was purified by HPLC using the conditions described in Example 21C to provide 47 mg (27% yield) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 2.71 (d, J=4.6 Hz, 3H), 5.18 (s, 2H), 6.50 (d, J=16.0 Hz, 1H), 6.91 (s, 2H), 7.00 (t, J=7.4 Hz, 1H), 7.08 (dd, J=8.8, 0.9 Hz, 2H), 7.35 (dd, J=8.8, 7.4 Hz, 2H), 7.52 (d, J=16.0 Hz, 1H), 8.10-8.13 (m, 2H), 8.14 (s, 1H); MS (ESI(+)) m/e 364.0 (M+H)+.

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