Water → Methyl (2S)-tert-butoxy[4-(4-chlorophenyl)-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of Methyl (2S)-tert-butoxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate (Preparation 16, 100 mg, 212 μmol) in dioxane (2 mL) was added 4-chlorobenzene boronic acid (66 mg, 422 μmol), ethyl-di-isopropyl-amine (120 μL, 636 μmol), water (500 μL) and palladium tetrakis(triphenylphosphine) (25 mg, 20 μmol). The reaction mixture was degassed and stirred at 100° C. in a sealed tube. The reaction was cooled to room temperature and diluted with ethyl acetate (10 mL). The mixture was passed through a pad of Celite. The organic filtrate was washed with water (10 mL) and brine (10 mL), dried over MgSO4 and concentrated in vacuo to yield the crude product. The residue was purified by flash chromatography eluting with ethyl acetate in heptane (0-6%) to give the title compound as a white semi-solid, 60 mg, in a 62% yield. 1H NMR (400 MHz, CDCl3) δ ppm 0.97 (s, 9H), 1.45-1.48 (m, 1H), 1.62-1.73 (m, 3H), 1.78-1.82 (m, 2H), 2.71 (s, 3H), 2.78-2.81 (m, 2H), 3.66 (s, 3H), 4.99 (s, 1H), 7.18-7.21 (m, 1H), 7.39-7.42 (m, 3H).

Provenance & Evidence