Toluene → 5-(2-Phenoxy-3-pyridinyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

A mixture of pinacol ester 31 (200 mg, 0.88 mmol), iodide 32 (390 mg, 1.32 mmol), LiCl (112 mg, 2.63 mmol), PdCl2(PPh3)2 (62 mg, 0.088 mmol), 1.0 M aq. Na2CO3 (2.2 mL, 2.19 mmol) in EtOH (4.0 mL) and toluene (4.0 mL) were refluxed for 5 h. After cooling the reaction mixture was partitioned between EtOAc/brine. The aqueous layer was extracted with more EtOAc (2×) and the combined organic extracts were dried (MgSO4) and concentrated. The residue was purified by silicagel chromatography using EtOAc:hexane (1:1) (gradient elution) to give 33 (106 mg, 42%); 1H NMR (400 MHz, CDCl3) δ 6.26 (bs, 4H), 6.55 (s, 1H), 7.38 (bs, 3H), 7.82 (s, 1H), 8.18 (s, 1H), 8.27 (s, 1H), 8.62 (s, 1H), 10.73 (bs, NH).

Provenance & Evidence