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5-Formylfuran-3-boronic acid → HCID 11590865, Verbindung

HRID 1454415
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1454415
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([C:11]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[C:23]([Cl:28])=[CH:22][C:21]=3[Cl:29])=[C:12]([C:17]#[N:18])[CH:13]=[N:14]2)=[CH:9][C:8]=1[O:30][CH3:31])(=O)=O.[CH:34]([C:36]1[O:37][CH:38]=[C:39](B(O)O)[CH:40]=1)=[O:35]>COCCOC.C(=O)(O)[O-].[Na+]>[Cl:29][C:21]1[CH:22]=[C:23]([Cl:28])[C:24]([O:26][CH3:27])=[CH:25][C:20]=1[NH:19][C:11]1[C:10]2[C:15](=[CH:16][C:7]([C:39]3[CH:40]=[C:36]([CH:34]=[O:35])[O:37][CH:38]=3)=[C:8]([O:30][CH3:31])[CH:9]=2)[N:14]=[CH:13][C:12]=1[C:17]#[N:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 52210965-Formylfuran-3-boronic acidHCID 234380223-Cyano-4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-quinolinyl trifluoromethanesulfonate

Produkt 1

HCID 11590865HCID 11590865, VerbindungAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80711,2-DimethoxyethaneLösungsmittelHCID 516892
Sodium Bicarbonate
Lösungsmittel

Versuchsvorschrift

A mixture of 3-cyano-4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-quinolinyl trifluoromethanesulfonate (835 mg, 1.60 mmol), 2-formyl-4-furan boronic acid (446 mg, 3.21 mmol), and tetrakis(triphenylphosphine)pallidium (0) (20 mg) in 40 mL of ethylene glycol dimethyl ether and 25 mL of saturated aqueous sodium bicarbonate is heated at reflux for 3 hours and then cooled to room temperature. The reaction mixture is partitioned between dichloromethane and water. The aqueous layer is extracted with 10% methanol in ethyl acetate. The organic layers are combined, dried over magnesium sulfate, filtered and concentrated in vacuo. Diethyl ether is added to the residue and the solid is collected by filtration to provide 723 mg of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-(5-formyl-3-furyl)-6-methoxy-3-quinolinecarbonitrile as a light yellow solid, mp 238-241° C.; 1H NMR (DMSO-d6) δ 3.88 (s, 3H), 4.09 (s, 3H), 7.38 (s, 1H), 7.76 (s, 1H), 8.01 (s, 1H), 8.29 (broad s, 2H), 8.48 (s, 1H), 8.77 (s, 1H), 9.71 (s, 1H), 9.87 (s, 1H); MS 468.0, 470.0 (M+H)+; HRMS calcd: 468.05124, found: 468.0511 (M+H)+.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. customThe reaction mixture is partitioned between dichloromethane and water
  4. extractionThe aqueous layer is extracted with 10% methanol in ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionDiethyl ether is added to the residue
  9. filtrationthe solid is collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-daec935a24104ae1a6fec31d443e094d
Quelldatensatz
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07479561B2

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