Sodium Carbonate → tert-butyl 4-(4-(3-(1-(3-cyanobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

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Reaction Steps

Using similar reaction conditions as described in step-ii of example-1, tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (intermediate 41) (200 mg, 0.3 mmol) was coupled with 3-((3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)benzonitrile (intermediate 55) (103 mg, 0.3 mmol) in sodium carbonate (98 mg, 0.9 mmol), PdCl2(dppf) (11 mg, 0.01 mmol), toluene/ethanol/water (2/2/1 ml) to give 80 mg (36% yield) of titled compound. 1H NMR (CD3OD, 400 MHz): δ8.44-8.43 (d, 1H), 7.85-7.84 (d, 1H), 7.55-7.49 (m, 5H), 7.38 (s, 1H), 7.09-7.07 (d, 2H), 6.60 (s, 1H), 5.41 (s, 2H), 3.27-3.24 (m, 4H), 3.11-3.09 (m, 4H), 2.21-2.17 (m, 6H). MS: m/z=488.1 (M+1), HPLC—92.75% (method-B).

Provenance & Evidence