Potassium Carbonate → HCID 86700301, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (75 mg, 0.151 mmol), KHCO3 (15.2 mg, 0.151 mmol), K2CO3 (41.7 mg, 0.302 mmol), 1-methyl-3-(4-methylpiperazin-1-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (55 mg, 0.154 mmol), Pd(PPh3)4 (17 mg, 15 μmol), H2O (400 μL), and dioxane (1.6 mL). The vessel was sealed and heated to 100° C. for 2 h. Then EtOH (absolute, 800 μL) and 2 M aq NaOH (400 μL) were added. Heating was continued at 100° C. for 3 h. The reaction was cooled to 23° C., and filtered (0.45 micron teflon syringe filter). The filtrate was purified by reverse phase HPLC, eluting by 5-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+: calc'd for C33H36ClN5O3S: 618.2, 620.2 (M+H+); Found: 618.3, 620.2 (M+H+). 1H NMR (400 MHz, CD3OD): δ 8.10 (s, 1H), 7.93-7.83 (m, 2H), 7.79-7.65 (m, 2H), 7.64-7.55 (m, 3H), 5.16 (s, 2H), 4.09 (d, J=12.9 Hz, 1H), 3.97 (s, 3H), 3.63 (d, J=8.7 Hz, 2H), 3.39 (d, J=11.5 Hz, 2H), 3.36-3.22 (m, 2H), 3.00 (s, 3H), 2.62 (s, 3H), 0.98 (s, 9H).

Provenance & Evidence