Acetyl chloride → Ethyl {4-[2-(allyloxy)-4-methylphenyl]-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl}(oxo)acetate hydrochloride salt

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To a stirred solution of [2-(allyloxy)-4-methylphenyl](2-amino-4,5,6,7-tetrahydro-1-benzothieno-3-yl)methanone (Step 5, 882 mg, 2.69 mmol) in ethanol (30 mL) was added ethyl 2,4-dioxopentanoate (378 μL, 2.69 mmol) followed by acetyl chloride (766 μL, 10.8 mmol), and the reaction was heated to 50° C. for 1 hour. The reaction was then concentrated in vacuo to give a mixture of diastereoisomers of the title compound as the hydrochloride salt, as a pale yellow oil, 1 g, in an 86% yield. LCMS (2 min acidic) 1.70 min 54-100% pure by UV, ES+/AP+ 450. 1HNMR (400 MHz, CDCl3) δ ppm 1.12 (t, 3H), 1.55-1.70 (m, 2H), 1.78-1.89 (m, 2H), 1.92-2.08 (m, 2H), 2.43 (, 3H), 2.87-2.93 (m, 2H), 2.95 (s, 3H), 3.84-3.94 (m, 2H), 4.39-4.51 (m, 2H), 5.09-5.20 (m, 2H), 5.82 (m, 1H), 6.76 (s, 1H), 6.87 (d, 1H), 6.95 (d, 1H).

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