Water → Methyl 2-(2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)phenyl)propanoate

HRID 865468Notizen

Reaktionsgleichung

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:20]([OH:23])[CH:21]=[CH2:22])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[Li]OC(C)=O.O.[Li+].[Cl-].I[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH:39]([CH3:44])[C:40]([O:42][CH3:43])=[O:41].C([O-])(O)=O.[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C:20](=[O:23])[CH2:21][CH2:22][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[CH:39]([CH3:44])[C:40]([O:42][CH3:43])=[O:41])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A degassed suspension of the product of Step 1 (15.0 g, 46.6 mmol), n-Bu4NCl (25.9 g, 93 mmol), LiOAc.circle-solid.H2O (7.7 g, 115 mmol), LiCl (1.98 g, 93 mmol), Pd(OAc)2 (0.315 g, 1.4 mmol), and methyl 2-(2-iodophenyl)propanoate in DMF (90 mL) was stirred for 2 hours at 100° C. The dark red solution was then cooled to 0° C. and poured into saturated NaHCO3 solution (500 mL). The product was extracted with EtOAc and the organic layer was washed with H2O followed by brine. The solvent was removed under vacuum and the residue was purified by flash chromatography (EtOAc:hexane 1:10, 1:5 and 3:10) to give a pale yellow foam (18.9 g).

Aufarbeitung

extractionThe product was extracted with EtOAc
washthe organic layer was washed with H2O
customThe solvent was removed under vacuum
customthe residue was purified by flash chromatography (EtOAc:hexane 1:10, 1:5 and 3:10)

Quellen und Nachweise

ORD-Eintrag: ord-b4765b3a5b4948698196192a1cf62365
Quelldatensatz: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05565473

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