Potassium Carbonate → 3-(1,3-benzothiazol-2-yl)-5-(1H-indol-2-yl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-benzothiazol-2-yl-5-bromopyridin-2-ylamine (BB7) (25 mg, 0.080 mmol), 1-Boc-indole-2-boronic acid (40 mg, 0.20 mmol) and potassium carbonate (34 mg, 0.24 mmol) in 1,4-dioxane (1.4 mL) and H2O (0.5 mL) was degassed and refilled with argon (3×) prior to the addition of Pd(dppf)Cl2 (6 mg, 0.01 mmol). The reaction mixture was degassed and refilled with argon (2×) and left to stir at 100° C. in the microwave reactor for 30 min. Then, the mixture was passed through PL-Thiol MP SPE resin and concentrated in vacuo. The residual oil was partitioned between DCM and H2O. The combined organic layers were treated with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting Boc-protected intermediate was left to stir in (1:1) DCM:TFA mixture (1.0 mL) at rt for 15 min. Purification via MDP afforded the title compound as a yellow solid. MS (ES+): m/z=343.08 (100) [MH+]. HPLC: tR=4.00 min (ZQ3, polar—5 min).

Provenance & Evidence