Sodium Carbonate → 5-bromo-3-(1-(2,5-difluorobenzyl)-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) (1 g, 2.37 mmol) was coupled with 1-(2,5-difluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Intermediate 6) (688 mg, 3.3 mmol) in sodium carbonate (749 mg, 7.07 mmol), bis(triphenyl phosphine)palladium(ii) dichloride (83 mg, 0.11 mmol) and toluene/ethanol/water (10/10/5 ml) to afford 550 mg (42.63% yield) of the pure product after column purification using 30% ethyl acetate in hexane as eluent. 1H NMR (DMSO-d6, 300 MHz): δ 8.59-8.51 (m, 3H), 8.29 (s, 1H), 8.13 (s, 1H), 7.98-7.95 (d, 2H), 7.42-7.40 (d, 2H), 7.35-7.10 (m, 4H), 5.52 (s, 2H), 2.33 (s, 3H). MS: m/z=542.6 (M−1).

Provenance & Evidence