4-Fluoroaniline → HCID 67346819, compound

Participants

Reaction Steps

Prepared from 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (34.84 mg, 0.1561 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), and 3-fluoro-4-(2-phenylthieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 76, Step A; 35 mg, 0.1040 mmol) according to the procedure for Example 73. The product was purified by preparative TLC eluting with EtOAc/MeOH (9:1). Isolated the product as a light yellow oil, which solidified upon standing (4.3 mg, 8%). 1H NMR (CDCl3, 400 MHz) δ 10.03 (s, 1H), 8.47 (d, J=5.5 Hz, 1H), 8.27 (s, 1H), 7.77 (m, 3H), 7.46 (m, 5H), 7.24 (m, 2H), 7.06 (d, J=9.0 Hz, 2H), 6.49 (m, 2H) 1.80, (m, 2H), 1.62 (m, 2H). LRMS (APCI pos) m/e 542 (M+1).

Provenance & Evidence