Potassium Carbonate → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indazol-6-yl)benzo[d]thiazol-6-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A vial was charged with (S)-ethyl 2-(2-(3-bromo-1-methyl-1H-indazol-6-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (36 mg, 57 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (13 mg, 57 mmol), KHCO3 (6.3 mg, 63 μmol), Pd(PPh3)4 (6.7 mg, 5.7 mmol), 2 M aq K2CO3 (250 mL), and dioxane (1 mL). The vessel was sealed and heated 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 C36H39ClN4O3S: 643.2, 645.2 (M+H+); Found: 643.0, 645.0 (M+H+). 1H NMR (400 MHz, CD3OD): δ 8.27 (s, 1H), 8.10 (d, J=8.7 Hz, 1H), 7.97-7.82 (m, 2H), 7.72-7.48 (m, 4H), 6.61 (s, 1H), 5.27 (s, 1H), 4.38-4.18 (m, 2H), 4.14 (s, 3H), 4.06-3.93 (m, 2H), 3.65-3.46 (m, 1H), 3.21-3.07 (m, 3H), 3.03 (s, 3H), 2.61 (s, 3H), 1.26 (t, J=7.1 Hz, 3H), 1.00 (s, 9H).

Provenance & Evidence