tert-Butyl carbazate → HCID 68472205, compound

Participants

Reaction Steps

A 100 ml flask is charged with 3-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde (Reference Example 9; 2.16 g, 10 mmol), hydrazinecarboxylic acid tert-butyl ester (1.32 g, 10 mmol), and methanol (10 ml). This mixture is heated at reflux for 18 hours, and then the solvent is removed on the rotavapor to leave the hydrazone (3.24 g, 98%). 1H-NMR (CDCl3, 300 MHz) δ 1.55 (s, 9H, C(CH3)3); 2.30 (s, 6H, N(CH3)2); 2.59, 2.87 (2 m, 2H each, CH2CH2NHMe2); 6.94 (d, 1H, J=2 Hz, H-2); 7.17 (d, 1H, J=8.5 Hz, H-7); 7.52 (dd, 1H, J=1.5 Hz, H-6); 7.68 (d, 1H, H-4); 7.84 (br s, 1H, N═CH); 8.42 (br s, NH); 9.10 (s, 1H, H-1). 13C-NMR (CDCl3, 75 MHz) δ 23.89 (CH2); 28.83 (C(CH3)3); 45.66 (N(CH3)2); 60.47 (CH2NMe2); 81.23 (OCMe3); 111.94 (C-7); 114.77 (C-3); 119.30 (C-4); 120.76 (C-6); 122.91 (C-2); 125.37 (C-5); 127.48 (C-9); 137.54 (C-8); 146.13 (N═CH); 153.13 (NC═O).

Provenance & Evidence