Hydrochloric Acid → Tert-butoxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

5-Benzothiazole-boronic acid (150 μmol) and ethyl-2-tert-butoxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate (Preparation 11, 1 mL of a 0.1M solution in dioxane, 100 μmol) were added to a reaction vial. A 1M solution of caesium carbonate (2004, 200 μmol) in water was then added, followed by 5 μmol of Pd(dppf)Cl2 and the whole stirred at 100° C. for 16 h before cooling to room temperature and evaporation of the solution under reduced pressure to give a yellow residue. A 2M solution of lithium hydroxide in water (2004, 400 μmol) was added to each vial, followed by 1 mL of THF, and the mixture was shaken at room temperature for 16 h. The pH of the solution was adjusted to neutral using a 1M aqueous solution of hydrochloric acid, before the mixture was evaporated to dryness under reduced pressure and the residue then purified by preparative HPLC on a C18 column, using a mixture of acetonitrile and water as the mobile phase. Evaporation of the appropriate fractions under reduced pressure provided the title compound (11 mg, 23%) as a white solid. ESI/APC(+): 467 (M+H).

Provenance & Evidence