Acetic Acid → HCID 86700209, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 6-bromo-N,N,1-trimethyl-1H-indazol-3-amine (102 mg, 0.402 mmol), bis-pinacolatodiboron (112 mg, 0.442 mmol), PdCl2(dppf).DCM (33 mg, 40 μmol), glacial AcOH (25 μL, 0.44 mmol), KOAc (130 mg, 1.33 mmol), and dioxane (2.0 mL). The reaction was heated to 100° C. for 30 min. To this reaction was added (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (150 mg, 0.302 mmol), 2 M aq K2CO3 (884 μL), and Pd(PPh3)4 (46 mg, 40 mop. The reaction was heated for another 1 h at 100° C. Finally, EtOH (absolute, 1.7 mL) and 2 M aqueous NaOH (884 μL) were added. The reaction was heated to 100° C. for another 1 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 C30H31ClN4O3S: 563.2, 565.2 (M+H+); Found: 563.2, 565.2 (M+H+). 1H NMR (400 MHz, CD3OD): δ 8.01 (s, 1H), 7.93 (d, J=8.6 Hz, 1H), 7.84 (s, 1H), 7.69 (dd, J=6.3, 3.2 Hz, 1H), 7.65 (dd, J=8.6, 1.2 Hz, 1H), 7.62-7.56 (m, 3H), 5.26 (s, 1H), 3.90 (s, 3H), 3.12 (s, 6H), 2.61 (d, J=4.8 Hz, 3H), 0.98 (d, J=4.1 Hz, 9H).

Provenance & Evidence