Sodium Carbonate → 5-bromo-3-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

Using similar reaction conditions as described in step-i of example-1,5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (Intermediate 1) (750 mg, 1.78 mmol) was coupled with 1-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Intermediate 5) (671 mg, 2.13 mmol) in sodium carbonate (614 mg, 4.4 mol), bis(triphenyl phosphine)palladium(ii) dichloride (62 mg, 2.13 mmol) and toluene/ethanol/water (10/10/5 ml) to afford 550.0 mg (57.95% yield) of the pure product after column purification using 30% ethyl acetate in hexane as eluent. 1H NMR (DMSO-d6, 300 MHz): δ 8.56-8.50 (m, 3H), 8.25 (s, 1H), 8.08 (s, 1H), 7.97-7.94 (d, 2H), 7.41-7.39 (d, 2H), 7.27-7.24 (d, 2H), 6.91-6.89 (d, 2H), 5.27 (s, 2H), 3.72 (s, 3H), 2.32 (s, 3H). MS: m/z=539.0 (M+2).

Provenance & Evidence