1-(Bromomethyl)-4-(trifluoromethyl)benzene → tert-Butyl-4-(2-{[4-(trifluoromethyl)benzyl]sulfonyl}thieno[3,2-c]pyridin-4-yl)piperazine-1-carboxylate

Participants

Reaction Steps

Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate (0.44 mmol) was treated with 4-(trifluoromethyl)benzylbromide (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 (16% over two steps). Beige solid. 1H NMR (300 MHz, CDCl3) δ 8.16 (d, J=6 Hz 1H), 7.53-7.61 (d, J=9 Hz 2H), 7.49 (s, 1H), 7.26-7.36 (m, 4H), 4.51 (s, 2H), 3.49-3.60 (m, 4H), 3.36-3.49 (m, 4H), 1.49 (s, 9H); MS (ESI+) for C24H26F3N3O4S2 m/z 542 (M+H)+. HPLC 71%, RT 4.07 min (ACE3 C8 50×4 mm, 5-50% acetonitrile in 3 min).

Provenance & Evidence