5-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one → HCID 178517360, compound

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Reaction Steps

The title compound (64 mg, 64%) was synthesized as a greenish yellow solid according to the method described for Example A67 (oil temp 75° C., reflux 2 h) using 5-bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (42.6 mg, 0.2 mmol) and (E)-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbaldehyde (49.8 mg, 0.2 mmol). 1H NMR indicated 7:6 mixture of E/Z isomers. 1H NMR (400 MHz, DMSO-d6) δ 8.57 (d, J=5.2 Hz, 2H), 8.34 (d, J=8.4 Hz, 1H), 8.26 (d, 1H), 8.22 (s, 1H), 8.12 (d, J=8.8 Hz, 1H), 8.03 (s, 1H), 7.93 (d, 1H), 7.89 (d, J=16.8 Hz, 1H), 7.72 (t, J=4.8 Hz, 2H), 7.55 (d, J=16.0 Hz, 1H); MS ESI 444.3 [M+H]+, calcd for [C22H14BrN5O+H]+ 444.0.

Provenance & Evidence