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

Participants

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) (300 mg, 0.455 mmol) was coupled with 1-(3-fluorobenzyl)-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 12) (187 mg, 0.592 mmol) in sodium carbonate (145 mg, 1.365 mmol), Pd(PPh3)2Cl2 (16 mg, 0.0227 mmol), Toluene/ethanol/water (5/10/1 ml) to give 250 mg (76.2% yield) of titled compound after purification by column (SiO2) using 20% ethyl acetate in hexane as eluent. 1H NMR (CDCl3, 300 MHz): δ 8.64 (s, 1H), 8.12-8.09 (d, 2H), 7.87 (s, 1H), 7.70 (s, 1H), 7.56 (s, 1H), 7.49-7.44 (m, 2H), 7.34-7.25 (m, 2H), 7.01-6.99 (m, 3H), 5.31 (s, 2H), 3.62-3.60 (t, 4H), 3.25-3.19 (t, 4H), 2.39 (s, 3H), 2.37 (s, 3H), 1.49 (s, 9H). MS: m/z=721.1 (M+1).

Provenance & Evidence