Acetic Acid → HCID 18367980, compound

Participants

Reaction Steps

To a solution of 2-[(3-tert-butyldimethylsilyloxymethyl)pyridine-2-carbonyl]-6-chloro-3-(propionylamino)indole (step 5, 544 mg, 1.15 mmol) and acetic acid (0.20 ml, 3.50 mmol) in THF (30 ml) was added tetra(n-butylammonium)fluoride (1M in THF, 3.5 ml, 3.50 mmol) at 0° C. The mixture was stirred for 4.5 h at the same temperature and diluted with diethyl ether (200 ml). This solution was washed with saturated aqueous sodium bicarbonate (50 ml), water (50 ml×2), and dried (MgSO4). Removal of solvent gave a crystalline residue. Recrystallization from ethyl acetate afforded 361 mg (88%) of the title compound. m.p.: 198-199° C. IR (KBr) ν: 3250, 1663, 1624, 1607, 1578, 1541, 1472, 1352, 1211, 1178, 1153, 1074, 1045, 1013, 833, 808, 716 cm−1 1H-NMR (CDCl3) δ: 11.33 (1 H, br s), 10.74 (1 H, br s), 8.75 (1 H, dd, J=1.6, 4.8 Hz), 8.47 (1 H, d, J=9.1 Hz), 8.00 (1 H, dd, J=1.5, 7.7 Hz), 7.57 (1 H, dd, J=4.8, 7.7 Hz), 7.36 (1 H, d, J=1.8 Hz), 7.05 (1 H, dd, J=1.8 and 9.1 Hz), 4.87 (2 H, d, J=7.3 Hz), 4.00 (1 H, t, J=7.1 Hz), 2.62 (2 H, q, J=7.6 Hz), 1.36 (3 H, t, J=7.6 Hz).

Provenance & Evidence