Sodium Carbonate → 1-Benzenesulfonyl-5-(2,3-dihydro-benzofuran-5-yl)-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

A mixture of 47 (200 mg, 0.308 mmol), EtOH (1.5 mL), toluene (1.5 mL), 2,3-dihydrobenzofuran-5-boronic acid (50 mg, 0.308 mmol), 1M aq. Na2CO3 (0.48 mL, 0.48 mmol), LiCl (25 mg, 0.619 mmol) and PdCl2(PPh3)2 (15 mg, 0.021 mmol) was refluxed for 1 h 40 min. The reaction mixture was concentrated to afford a pale yellow solid, which was purified by silicagel chromatography using 30% ethyl acetate in hexane as eluent (gradient elution) to give the product 48 (187 mg, 86%) as a pale yellow solid; 1H NMR (400 MHz, CDCl3) δ 3.27 (t, J=17.2, 8.6 Hz, 2H), 4.61 (t, J=17.4, 8.7 Hz, 2H), 6.86 (d, J=8.2 Hz, 1H), 7.19-7.23 (m, 7H), 7.33-7.36 (m, 10H), 7.45 (t, J=15.3, 7.26 Hz, 2H), 7.54-7.58 (m, 1H), 7.65 (s, 1H), 7.74 (s, 1H), 7.89 (d, J=2.1 Hz, 1H), 7.97 (s, 1H), 8.19-8.21 (m, 2H), 8.60 (d, J=2.1 Hz, 1H).

Provenance & Evidence