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

HRID 549295

Reaktionsgleichung

Reaktionsgleichung von HRID 549295
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+].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>C(#N)C>[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][N:37]([C:2]2[C:7]3[CH:8]=[C:9]([S:11]([CH2:20][C:19]4[CH:22]=[CH:23][CH:24]=[C:17]([C:16]([F:26])([F:25])[F:15])[CH:18]=4)(=[O:13])=[O:12])[S:10][C:6]=3[CH:5]=[CH:4][N:3]=2)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Komponenten

5

Edukt 3

HCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86591057Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate

Produkt 1

HCID 67156769tert-Butyl-4-(2-{[3-(trifluoromethyl)benzyl]sulfonyl}thieno[3,2-c]pyridin-4-yl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate (0.44 mmol) was treated with 3-(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 0.023 g (10% over two steps). Beige solid. 1H NMR (300 MHz, CDCl3) δ 8.14 (d, J=6 Hz, 1H), 7.85-7.91 (m, 1H), 7.61-7.72 (m, 2H), 7.50-7.60 (m, 1H), 7.12-7.31 (m, 2H), 4.74 (s, 2H), 3.52-3.71 (m, 8H), 1.50 (s, 9H); MS (ESI+) for C24H26F3N3O4S2 m/z 542 (M+H)+. HPLC 85%, RT 2.13 min (YMC ODS AQ, 33×3 mm, 10-90% acetonitrile in 3 min).

Quellen und Nachweise

ORD-Eintrag
ord-1ca7e45b3e814d00b2ea2ffa86c8fce8
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943639B2

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