HCID 178418361, compound → HCID 178516889, compound

Participants

Reaction Steps

To a solution of 158b (0.29 g, 1.01 mmol) in CH2Cl2:EtOAc:MeOH (2:2:1, 10 mL) was added 10% Pd on carbon (15 mg). Reaction was stirred under balloon hydrogen pressure for 5 h. Reaction mixture was filtered and solvent was evaporated. Column chromatography using gradient CH2Cl2:Acetone (max 20%) gave pure 159b (0.19 g, 64%) as a slightly brownish solid. 1H NMR (400 MHz, DMSO) δ 9.03 (s, 1H), 8.62 (s, 1H), 7.82 (d, J=7.6 Hz, 2H), 7.38 (m, 3H), 7.15 (d, J=6.6 Hz, 1H), 6.68 (d, J=6.4 Hz, 1H), 6.11 (t, J=6.7 Hz, 1H), 4.43 (t, J=6.4 Hz, 2H), 3.99 (m, 2H), 2.27 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 147.49, 129.71, 128.52, 127.99, 125.29, 120.42, 107.98, 66.61, 47.10, 29.27. (expected aromatic carbons=11; quaternary carbons can't be seen even after repeated cycles) HRMS (EI) calcd for C16H16N4O2 [M]+ 296.1273. found 296.1274.

Provenance & Evidence