1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59596491, compound

Participants

Reaction Steps

A degassed solution of 1-methyl-3-(nonafluorobutane-1-sulfonyloxy)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (500 mg, 0.99 mmol), 4-bromo-2-chloroaniline (246 mg, 1.19 mmol), Pd2dba3 (91 mg, 0.10 mmol), Xantphos (114 mg, 0.20 mmol) and DBU (352 μl, 2.48 mmol) in toluene (8 ml) was subjected to microwave irradiation at 120° C. for 5 minutes. The reaction mixture was cooled to ambient temperature then diluted with ethyl acetate (100 ml). The resultant solution was washed with water (30 ml), dried (Na2SO4) and concentrated in vacuo to give an oil. The oil was purified by flash chromatography (Si-PPC, cyclohexane:ethyl acetate, gradient 90:10 to 0:100) to afford the title compound as a yellow solid (140 mg, 35%). 1H NMR (CDCl3, 400 MHz) 8.75 (d, J=1.0 Hz, 1H), 8.41 (d, J=6.1 Hz, 1H), 7.68 (s, 1H), 7.54 (d, J=2.3 Hz, 1H), 7.19-7.27 (m, 2H), 6.94 (d, J=8.8 Hz, 1H), 4.44 (q, J=7.2 Hz, 2H), 3.99 (s, 3H), 1.44 (t, J=7.2 Hz, 3H).

Provenance & Evidence