4-Fluoroaniline → HCID 67348732, compound

Participants

Reaction Steps

Prepared from 4-(2-(3-(diethylamino)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-2-methylbenzenamine (0.070 g, 0.1322 mmol), and 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (0.04424 g, 0.1982 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 73. The crude was purified by preparative TLC eluting with EtOAc/MeOH (9:1). The product was a light yellow oil (3.9 mg, 5%). 1H NMR (CDCl3, 400 MHz) δ 9.19 (s, 1H), 8.88 (s, 1H), 8.47 (d, J=5.5 Hz, 1H), 7.87 (d, J=9.8 Hz, 1H), 7.57 (s, 1H), 7.48 (m, 2H), 7.04 (m, 4H), 6.58 (d, J=5.5 Hz, 1H), 3.73 (s, 2H), 2.68 (q, J=7, 14 Hz, 4H), 2.34 (s, 3H) 1.73 (m, 4H), 1.15 (t, J=7.2 Hz, 6H). LRMS (APCI pos) m/e 571 (M+1).

Provenance & Evidence