Sodium Hydroxide → 5-(4-(4-Phenoxyphenylamino)-quinolin-7-yl)thiazole-4-carbaldehyde

HRID 1403761

Reaktionsgleichung

Reaktionsgleichung von HRID 1403761
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21](I)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:26]1CCO[CH:27]1[C:31]1[N:32]=[CH:33][S:34][C:35]=1[Sn](CCCC)(CCCC)CCCC.[OH-].[Na+]>C1COCC1.Cl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Ag]=O>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:35]4[S:34][CH:33]=[N:32][C:31]=4[CH:27]=[O:26])=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 3

HCID 14798Sodium HydroxideHCID 21952018(4-Phenoxyphenyl)-(7-iodoquinolin-4-yl)amineHCID 219520694-(1,3-Dioxolan-2-yl)-5-tributylstannylthiazole

Produkt 1

HCID 542040185-(4-(4-Phenoxyphenylamino)-quinolin-7-yl)thiazole-4-carbaldehydeAusbeute 40,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 92152Silver(II) oxideKatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Prepared according to Procedure B from (4-phenoxyphenyl)-(7-iodoquinolin-4-yl)amine (0.876 g, 2 mmol), 4-(1,3-dioxolan-2-yl)-5-tributylstannylthiazole (2.1 mmol), bis(triphenylphosphine) palladium (II) chloride (0.105 g, 0.15 mmol, 7.5 mol %) and silver oxide (0.463 g, 2 mmol) heated under reflux under nitrogen for 18 hr. The reaction mixture was then filtered through Harborlite® and the filtrate was concentrated. The product was purified on Bond Elut™ cartridge, eluting sequentially with dichloromethane, chloroform, diethyl ether and ethyl acetate. The ketal (0.385 g, 0.824 mmol) was stirred at room temperature in a mixture of THF (10 ml) and 1N HCl (10 ml) for 2 hr. The suspension was basified with 2N NaOH (5 ml) and the THF was removed. The aqueous suspension was filtered and washed with water to give the product as a yellow solid (0.346 g); m/z 424.

Aufarbeitung

  1. customPrepared
  2. temperatureheated
  3. temperatureunder reflux under nitrogen for 18 hr
  4. filtrationThe reaction mixture was then filtered through Harborlite®
  5. concentrationthe filtrate was concentrated
  6. customThe product was purified on Bond Elut™ cartridge
  7. washeluting sequentially with dichloromethane, chloroform, diethyl ether and ethyl acetate
  8. customthe THF was removed
  9. filtrationThe aqueous suspension was filtered
  10. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-794bfd5bc4c64aa094ce3a2215cc1519
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912205B2

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