Toluene → HCID 67348445, compound

Participants

Reaction Conditions

Reaction Steps

A vigorously stirred mixture of cesium carbonate (190 mg, 0.583 mmol), 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 150 mg, 0.388 mmol), phenylboronic acid (59.2 mg, 0.486 mmol), toluene (4 mL) and EtOH (1 mL) was degassed under nitrogen for 10 minutes, and then Pd(PPh3)4 (22.4 mg, 0.0194 mmol) was added. The reaction mixture was heated at 80° C. for 18 hours, then cooled to room temperature and diluted with water (20 mL). The reaction mixture was extracted with EtOAc, and the organic layer was dried organic over sodium sulfate, filtered and concentrated. The residue was purified on a Biotage 40S (2:1 EtOAc/Hexane). The product was a light orange solid (75 mg, 53%). 1H NMR (CDCl3, 400 MHz) δ 8.46 (d, J=5.5 Hz, 1H), 7.75 (m, 3H), 7.46 (t, J=7.2 Hz, 2H), 7.40 (m, 1H), 7.06 (t, J=8.8 Hz, 1H), 6.54 (m, 1H), 6.50 (m, 2H), 3.84 (br s, 2H). LRMS (ESI pos) m/e 337 (M+1).

Provenance & Evidence