Benzyl Bromide → tert-Butyl-4-[2-(benzylsulfonyl)thieno[3,2-c]pyridin-4-yl]piperazine-1-carboxylate

HRID 549300

Reaction equation

HRID 549300 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[C:9]([S:11]([O-:13])=[O:12])[S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[Li+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(#N)C>[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][N:33]([C:2]2[C:7]3[CH:8]=[C:9]([S:11]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)(=[O:13])=[O:12])[S:10][C:6]=3[CH:5]=[CH:4][N:3]=2)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86591057Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate

Product 1

HCID 67157171tert-Butyl-4-[2-(benzylsulfonyl)thieno[3,2-c]pyridin-4-yl]piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate (0.44 mmol) was treated with 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 0.00 g (7% over two steps). Beige solid. 1H NMR (300 MHz, CDCl3) δ 8.14 (d, J=5.5 Hz 1H), 7.27-7.40 (m, 5H), 7.15-7.21 (m, 2H), 4.45 (s, 2H), 3.50-3.56 (m, 4H), 3.40-3.45 (m, 4H), 1.49 (s, 9H); MS (ESI+) for C23H27N3O4S2 m/z 474 (M+H)+. HPLC 77%, RT 3.93 min (ACE3 C8 50×4 mm, 5-50% acetonitrile in 3 min).

Sources & evidence

ORD record
ord-96d662fe13e74bad8b74193eb836266d
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Linked notes

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