Water → 3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)aniline

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of NaH (0.432 g, 18.0 mmol) in DMSO (30 mL) was carefully added 4-amino-2-fluorophenol (1.91 g, 15.0 mmol) in portions. The reaction was stirred under N2 for 15 minutes. 7-Chlorothieno[3,2-b]pyridine (2.54 g, 15.0 mmol) was added as a solid. The reaction was heated to 100° C. for 2 hours. The reaction was allowed to cool to room temperature, and water (40 mL) was carefully added. The suspension was filtered. The brown solid was washed with water (2×10 mL), and dried by toluene azeotrope (5×20 mL) by rotary evaporation at 50° C. The solid was recrystallized from hot toluene (10 mL) to obtain a brown, crystalline solid (2.64 g, 68%). 1H NMR (400 MHz, CDCl3) δ 8.49 (d, J=6 Hz, 1H), 7.73 (d, J=6 Hz, 1H), 7.56 (d, J=6 Hz, 1H), 7.04 (t, J=9 Hz, 1H), 6.51 (m, 3H), 3.83 (br s, 2H). LRMS (APCI pos) m/e 261 (M+1).

Provenance & Evidence