Potassium Carbonate → ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(3-(tert-butylamino)-6-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate

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Reaction Steps

This compound (230 mg, 0.44 mmol, 58% yield) as a yellow foam was prepared according to the procedures described for Intermediate 293b, using 2-bromo-1-(3-(tert-butylamino)-6-fluoro-2-methylquinoxalin-5-yl)ethanone (605) (268 mg, 0.76 mmol), ethyl 3-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-3-oxopropanoate (604) (619 mg, 2.28 mmol) and K2CO3 (525 mg, 3.80 mmol) in EtOH (2 mL) and THF (2 mL) was stirred at RT for 2 days, followed by subsequent treatment of the resulting 295a (light-yellow oil, m/z (ESI, +ve) 545.2 (M+H)+) with NH4OAc (469 mg, 6.08 mmol) in EtOH (5 mL) and HOAc (3 mL) at 60° C. for 18 h. 1H NMR (400 MHz, CDCl3) δ ppm 7.64 (dd, J=8.90, 5.97 Hz, 1H), 7.17 (dd, J=11.74, 9.00 Hz, 1H), 4.86 (s, 1H), 4.34 (q, J=7.04 Hz, 2H), 2.52 (s, 3H), 1.64 (s, 9H), 1.40 (t, J=7.14 Hz, 3H), 1.36 (s, 9H), 1.20-1.33 (m, 4H). 19F NMR (376 MHz, CDCl3) δ ppm −109.93 (s, 1F). m/z (ESI, +ve) 526.2 (M+H)+.

Provenance & Evidence