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

Participants

Reaction Conditions

Reaction Steps

To a vial flushed with argon was added (S)-methyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (100 mg, 0.207 mmol), 1-methyl-3-(pyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (83.3 mg, 0.25 mmol), Pd(PPh3)4 (24 mg, 21 mmol), and K2CO3 (86 mg, 0.62 mmol). De-gassed dioxane (2 mL) and water (0.5 mL) were then added, and the reaction was heated to 100° C. for 1 h. After cooling to rt, the reaction was filtered over a plug of Celite, concentrated, and purified by column chromatography (gradient 0 to 40% EtOAc in hexanes) to give the product. 1H NMR (400 MHz, CDCl3) δ 9.21-9.15 (m, 1H), 8.84-8.77 (m, 1H), 8.25 (dd, J=8.8, 1.7 Hz, 1H), 8.14 (d, J=8.0 Hz, 1H), 7.88 (s, 1H), 7.78 (td, J=7.7, 1.7 Hz, 1H), 7.59-7.49 (m, 4H), 7.47 (d, J=8.9 Hz, 1H), 7.29-7.24 (m, 1H), 5.21 (s, 1H), 4.17 (s, 3H), 3.75 (s, 3H), 2.59 (s, 3H), 0.98 (s, 9H).

Provenance & Evidence