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

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Reaction Conditions

Reaction Steps

A mixture of iodide 55 (0.083 g, 0.18 mmol), (1-trityl-1H-pyrazol-4-yl)boronic acid (0.094 g, 0.27 mmol), PdCl2(PPh3)2 (0.012 g, 0.017 mmol), LiCl (0.022 g, 0.52 mmol) and 1.0 M aqueous Na2CO3 solution (0.442 mL, 0.442 mol) in EtOH (2 mL)-toluene (2 mL) was stirred at 105° C. for 2 hours. The mixture was cooled and the organic layer was poured into water and extracted with AcOEt. The organic extract was washed with brine, dried (MgSO4), and concentrated to afford a syrup. The syrup was purified by means of preparative TLC with hexane:AcOEt as eluent to afford 56 (0.093 g, 81%) as a tan syrup. 1H NMR (400 MHz, CDCl3) δ 2.97-3.02 (m, 4H), 3.77-3.82 (m, 4H), 7.11-7.16 (m, 6H), 7.24-7.29 (m, 8H), 7.35-7.40 (m, 2H), 7.44-7.49 (m, 1H), 7.51 (d, J=0.08 Hz, 1H), 7.61 (s, 1H), 7.86 (d, J=0.08 Hz, 1H), 8.06-8.09 (m, 2H), 8.13 (d, J=0.26 Hz, 1H).

Provenance & Evidence