Potassium Fluoride → Ethyl 4-[6-amino-5-(1,3-benzothiazol-2-yl)pyridin-3-yl]phenoxyacetate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-benzothiazol-2-yl-5-bromopyridin-2-ylamine (BB7) (100 mg, 0.330 mmol), 4-(2-ethoxy-2-oxoethoxy)benzeneboronic acid (100 mg, 0.600 mmol) and potassium fluoride (57 mg, 0.98 mmol) in 1,4-dioxane (9.0 mL) and H2O (3.0 mL) was degassed and refilled with argon (3×) prior to the addition of Pd(dppf)Cl2 (10 mg, 0.020 mmol). The reaction mixture was degassed and refilled with argon (2×) and left to stir at 100° C. for 2 h. The mixture was quickly passed through a silica gel pad (5% MeOH in DCM), which afforded the title compound as a yellow solid. MS (ES+): m/z=406.10 (100) [MH+]. HPLC: tR=3.90 min (ZQ3, polar—5 min).

Provenance & Evidence