3-Chlorophenethylamine → 6-{1-[2-(3-Chloro-phenyl)-ethylamino]-indan-5-yloxy}-nicotinamide

Participants

Reaction Steps

Using a method similar to Example 1, using 6-(1-oxo-indan-5-yloxy)nicotinamide (Intermediate 4, 905 mg, 3.00 mmol), 2-(3-chlorophenyl)ethylamine (560 mg, 3.60 mmol), Ti(iPrO)4 (1.70 g, 6.00 mmol), TiCl4 (1.0M/DCM, 6.00 ml, 6.00 mmol), and NaBH3CN (377 mg, 6.00 mmol) gives the title compound (738 mg) as a white solid. Mass spectrum (ion spray): m/z=408 (M+1); 1HNMR (CDCl3): 8.58 (s, 1H), 8.15 (d, 1H), 7.31 (d, 1H), 7.25-7.18 (m, 3H), 7.11 (d, 1H), 6.98-6.93 (m, 3H), 5.89 (br. s, 2H), 4.26 (t, 1H), 3.03-2.96 (m, 3H), 2.87-2.78 (m, 3H), 2.44 (m, 1H), 1.85 (m, 1H).

Provenance & Evidence