4-Fluoroaniline → HCID 67347260, compound

Participants

Reaction Steps

Prepared from 4-(2-(3-(diethylamino)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-2-methylbenzenamine (50 mg, 0.14 mmol), and 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (46 mg, 0.21 mmol; prepared from cyclopropane-1,1-dicarboxylic acid and 4-fluoroaniline using the methods described in WO 2005/030140 and by Shih and Rankin, Synth. Comm. 1996, 26(4), 833-836) according to the procedure for Example 74. The crude was purified by preparative TLC eluting with EtOAc/MeOH (9:1). The product was a light yellow oil (0.8 mg, 1%). 1H NMR (CDCl3, 400 MHz) δ 9.21 (s, 1H), 8.70 (s, 1H), 8.45 (d, J=5.5 Hz, 1H), 7.57 (s, 1H), 7.48 (m, 4H), 7.06 (m, 3H), 6.41 (d, J=5.5 Hz, 1H), 3.71 (s, 2H), 2.65 (q, J=7, 14 Hz, 4H), 2.17 (s, 3H), 1.71 (m, 4H), 1.13 (t, J=7.0 Hz, 6H). LRMS (APCI pos) m/e 571 (M+1).

Provenance & Evidence