Water → HCID 58710037, compound

Participants

Reaction Steps

To a mixture of 4-[4-(benzothiazol-6-ylamino)-5-bromo-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (20 mg, 0.038 mmol), DPPF (10.1 mg, 0.018 mmol), water (0.04 mL) and zinc cyanide (8.9 mg, 0.075 mmol) in acetonitrile-(4 mL) was added Pd2 dba3 (7.0 mg, 0.007 mmol) and the mixture was heated to reflux under N2 overnight. The reaction mixture was evaporated, and the crude product was purified by preparative TLC using 7% methanol in DCM as eluent to afford the title compound as light gray solid. 1H NMR (400 MHz, CDCl3): δ=8.98 (s, 1H), 8.22 (s, 1H), 8.10 (d, J=8.6 Hz, 1H), 7.78 (d, J=2.0 Hz, 1H), 7.36 (dd, J=8.6, 2.1 Hz, 1H), 6.95 (s, 1H), 5.93 (bs, 1H), 5.36 (s, 1H), 3.99-4.02 (m, 2H), 3.44 (t, J=5.7 Hz, 2H), 3.42 (d, J=4.9 Hz, 2H), 2.07-2.12 (m, 2H), 1.39 (s, 9H); MS (ES+): m/z 472.96 (100) [MH+]; HPLC: tR=3.25 min (ZQ2000, polar—5 min).

Provenance & Evidence