tert-Butyl piperazine-1-carboxylate → tert-Butyl 4-{2-[(3,5-dimethoxybenzyl)sulfonyl]thieno[3,2-c]pyridin-4-yl}piperazine-1-carboxylate

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Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate (0.44 mmol) was treated with 3,5-dimethoxybenzylbromide (0.59 mmol) as described in Method P above and then reacted further with tert-butyl-piperazine-1-carboxylate as described in Method Q. Yield 0.02 g (10% over two steps). Beige solid. 1H NMR (300 MHz, CDCl3) δ 8.14-8.18 (m, 1H), 7.55 (s, 1H), 6.40-6.45 (m, 1H), 6.26-6.34 (m, 2H), 4.39 (s, 2H), 3.54-3.72 (m, 14H), 1.50 (s, 9H); MS (ESI+) for C25H31N3O6S2 m/z 534 (M+H)+. HPLC 69%, RT 1.99 min (YMC ODS AQ, 33×3 mm, 10-90% acetonitrile in 3 min).

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