HCID 68472205, compound → HCID 58882797, compound

Participants

Reaction Conditions

Reaction Steps

A 50 ml pressure vessel is charged with N′-[3-(2-Dimethylamino-ethyl)-1H-indol-5-ylmethylene]-hydrazinecarboxylic acid tert-butyl ester (Example 11; 1.20 g, 3.63 mmol), ethanol (18 ml), and the catalyst (5% Pd/C type E-4522, 240 mg). The vessel is sealed, purged with argon (three times and hydrogen (three times), heated in an oil bath to 87° C., and then pressurized with hydrogen (43.4 bar). The stirrer is started (900 rpm), and the hydrogenation allowed to proceed for 18 hours. After cooling to ambient temperature the pressure vessel is vented, and the reaction mixture filtered over a pad of Hyflo to remove the catalyst. Removal of the solvent gives the product (1.092 g, 90.4%) as a pale yellow residue, which is pure by NMR. 1H-NMR (CD3OD, 300 MHz) δ 1.33 (s, 9H, C(CH3)3); 2.45 (s, 6H, N(CH3)2); 2.84-2.96 (m, 4H, CH2CH2NMe2); 3.88 (s, 2H, CH2N); 7.00 (br s, 1H, H-2); 7.02 (dd, 1H, J=8.3 Hz, J=1.5 Hz, H-6); 7.21 (d, 1H, H-7); 7.45 (s, 1H, H-4). 13C-NMR (CD3OD, 75 MHz) δ 23.69 (CH2); 29.11 (C(CH3)3); 45.03 (N(CH3)2); 57.94 (CH2N); 60.66 (CH2NMe2); 112.41 (C); 112.74 (CH); 120.30 (CH); 124.53 (CH); 128.89 (C); 129.15 (C); 138.17 (C); 162.32 (br, C═O).

Provenance & Evidence