3-Buten-1-ol → 4-Hydroxy-3-[4-(4-hydroxy-but-1-enyl)-phenyl]-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile

HRID 1244115

Reaktionsgleichung

I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([OH:17])=[C:14]([C:18]#[N:19])[C:13](=[O:20])[NH:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:43]([OH:47])[CH2:44][CH:45]=[CH2:46]>CC([O-])=O.CC([O-])=O.[Pd+2].C(N(CC)CC)C>[OH:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH:46]=[CH:45][CH2:44][CH2:43][OH:47])=[CH:3][CH:4]=3)=[CH:9][S:10][C:11]=2[NH:12][C:13](=[O:20])[C:14]=1[C:18]#[N:19]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To a stirred suspension of 3-(4-iodo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (60 mg, 0.15 mmol), triethylamine (0.1 mL), Pd(OAc)2 (3 mg), P(o-Tol)3 (9 mg), and MgO (18 mg, 0.45 mmol) was added 0.1 mL of but-3-en-1-ol in a single portion. The resulting mixture was heated to 150° C. using microwave reactor for 20 min, then filtered, concentrated and purified by reverse phase HPLC to give the titled compound. MS (ESI) m/e 399 (M+H)+; 1H NMR (500 MHz, DMSO-d6): δ 2.35 (q, J=5 Hz, 2H), 3.53 (t, J=5 Hz, 2H), 6.28 (dt, J=15.91, 7.02 Hz, 1H), 6.45 (d, J=15.91 Hz, 1H), 6.60 (s, 1H), 7.27 (d, J=8.42 Hz, 2H), 7.39 (d, J=8.11 Hz, 2H).

Aufarbeitung

customfor 20 min
filtrationfiltered
concentrationconcentrated
custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag: ord-0e9f92b031744202b10945f8af7b36da
Quelldatensatz: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07119205B2

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