Dichloromethane → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-cyclopropyl-1-methyl-1H-indazol-5-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 5-bromo-3-cyclopropyl-1-methyl-1H-indazole (49 mg, 0.19 mmol), bis-pinacolatodiboron (53 mg, 0.21 mmol), PdCl2(dppf).DCM (15 mg, 19 μmol), KOAc (62 mg, 0.62 mmol), and dioxane (1.6 mL). The reaction was sealed and heated to 100° C. for 2 h. (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (94 mg, 0.190 mmol), Pd(PPh3)4 (22 mg, 19 μmol), and 2 M aq K2CO3 (400 μL) were added; the reaction was heated at 100° C. for 1.5 h. The reaction was treated with absolute EtOH (2 mL) and 10 M aq NaOH (2 mL). After heating to 100° C. for 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 C31H30ClN3O3S: 560.2, 562.2 (M+H+); Found: 560.2, 562.2 (M+H+). 1H NMR (400 MHz, CD3OD): δ 8.37 (s, 1H), 7.99 (dd, J=8.8, 1.3 Hz, 1H), 7.77 (s, 1H), 7.72-7.66 (m, 1H), 7.58 (d, J=3.2 Hz, 3H), 7.49 (d, J=8.9 Hz, 1H), 5.25 (s, 1H), 3.93 (s, 3H), 2.59 (s, 3H), 2.26 (ddd, J=13.1, 8.3, 5.2 Hz, 1H), 1.16-0.98 (m, 4H), 0.97 (s, 9H).

Provenance & Evidence