3-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline → N-(3-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)prop-2-ynyl)-2-(pyrrolidin-1-yl)acetamide

Participants

Reaction Steps

Prepared from 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 72 mg, 0.186 mmol) and N-(prop-2-ynyl)-2-(pyrrolidin-1-yl)acetamide (34 mg, 0.205 mmol; prepared according to the method described in WO 04/076412A) according to the procedure described for Example 6, Step B, except the reaction was executed at room temperature for 3 hours. The product was purified by preparative TLC (10% MeOH/CH2Cl2). The product was obtained as a waxy solid (69 mg, 65%). 1H NMR (400 MHz, CDCl3) δ 8.48 (d, J=6 Hz, 1H), 7.60 (s, 1H), 7.52 (br s, 1H), 7.03 (t, J=9 Hz, 1H), 6.54 (m, 2H), 6.48 (m, 1H), 4.39 (d, J=6 Hz, 2H), 3.86 (br s, 2H), 3.28 (s, 2H), 2.69 (m, 4H), 1.85 (m, 4H). LRMS (ESI pos) m/e 425 (M+1).

Provenance & Evidence