Potassium Carbonate → HCID 86700292, 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 (100 mg, 0.202 mmol), 1,3-dimethylindazole-5-boronic acid (42 mg, 0.22 mmol), Pd(PPh3)4 (23 mg, 20 μmol), 2 M aq K2CO3 (800 μL), and dioxane (3.2 mL). The reaction was heated to 100° C. for 2 h. The reaction was treated with absolute EtOH (1.6 mL) and 10 M aq NaOH (800 μL). After heating to 100° C. for 2 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 C29H28ClN3O3S: 534.2, 536.2 (M+H+). Found: 534.3, 536.3 (M+H+). 1H NMR (400 MHz, CD3OD): δ 8.35 (s, 1H), 8.08 (dd, J=8.9, 1.6 Hz, 1H), 7.81 (s, 1H), 7.75-7.64 (m, 1H), 7.62-7.52 (m, 4H), 5.26 (s, 1H), 4.01 (s, 3H), 2.61 (s, 3H), 2.57 (s, 3H), 0.98 (s, 9H).

Provenance & Evidence