3-Bromobenzyl bromide → tert-Butyl-4-{2-[(3-bromobenzyl)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 3-bromobenzylbromide (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 0.023 g (10% over two steps). Beige solid. 1H NMR (300 MHz, CDCl3) δ 8.16 (d, J=6 Hz, 1H), 7.50-7.55 (m, 2H), 7.32-7.40 (m, 2H), 7.10-7.24 (m, 3H), 4.44 (s, 2H), 3.61-3.73 (m, 8H), 1.50 (s, 9H); MS (ESI+) for C23H26BrN3O4S2 m/z 554 (M+H)+. HPLC 77%, RT 4.07 min (ACE3 C8 50×4.6 mm, 5-50% acetonitrile in 3 min).

Provenance & Evidence