Sodium hydride → N-(1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(prop-1-en-2-yl)benzamide

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Reaction Steps

In a 50 mL pear flask were added 1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-amine, TFA (1I, 5.2 g, 19 mmol) in pyridine (200 ml). At 0° C., 4-(prop-1-en-2-yl)benzoyl chloride (3.8 g, 21 mmol) was added. After 15 minutes, sodium hydride (0.53 g, 13 mmol) was added, and the reaction was stirred at room temperature for four hours. At 0° C., an additional 0.55 equivalent of 4-(prop-1-en-2-yl)benzoyl chloride was added and the reaction mixture was let stirred for another 15 hours at room temperature. The reaction was quenched by adding saturated NaHCO3 at 0° C. and stirred for 30 minutes. Volatiles were removed in vacuo, and the residue was extracted with ethyl acetate twice. Combined organic layers were dried over MgSO4, filtered and concentrated. The crude mixture was then purified by normal phase column chromatography (SiO2, eluting 20-50% EtOAc) to give the desired product N-(1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(prop-1-en-2-yl)benzamide (5A, 4.7 g, 15 mmol, 81% yield). 1H NMR (DMSO-d6) δ: 10.61 (s, 4H), 8.64 (s, 4H), 8.32 (s, 4H), 8.04-8.10 (m, 9H), 7.62-7.67 (m, 9H), 7.47 (d, J=3.3 Hz, 4H), 6.57 (dd, J=3.2, 0.9 Hz, 5H), 5.58 (s, 4H), 5.23 (t, J=1.4 Hz, 4H), 4.21 (q, J=7.2 Hz, 9H), 2.16 (d, J=0.5 Hz, 13H), 1.39 (t, J=7.2 Hz, 3H); m.p. 125-8° C.

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