2-Formyl-4-(tributylstannyl)thiazole → 4-(4-(4-Phenoxyphenylamino)-quinolin-7-yl) thiazole-2-carbaldehyde

HRID 2086965

Reaktionsgleichung

Reaktionsgleichung von HRID 2086965
[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.C([Sn](CCCC)(CCCC)[C:31]1[N:32]=[C:33]([CH:36]=[O:37])[S:34][CH:35]=1)CCC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[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:31]4[N:32]=[C:33]([CH:36]=[O:37])[S:34][CH:35]=4)=[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

5

Edukt 2

HCID 164271112-Formyl-4-(tributylstannyl)thiazoleHCID 21952018(4-Phenoxyphenyl)-(7-iodoquinolin-4-yl)amine

Produkt 1

HCID 219519814-(4-(4-Phenoxyphenylamino)-quinolin-7-yl) thiazole-2-carbaldehydeAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Prepared according to Procedure B from (4-phenoxyphenyl)-(7-iodoquinolin-4-yl)amine (2 g, 4.56 mmol), 4-(tributylstannyl)thiazole-2-carbaldehyde (1.84 g,4.56 mmol) and dichlorobis(triphenylphosphine)palladium (II) (0.74 g, 20 mol%) heated at reflux overnight (18 hrs) in dioxane (50 ml). The cooled solution was filtered through a plug of Celite®, concentrated and triturated with iso-hexane (3×20 ml). The resultant solid was purified via flash column chromatography on silica gel, eluting with 5% methanol in chloroform. The purified product was isolated as a yellow solid (0.85 g, 44%). δH [2H6] DMSO 10.10(1H,s), 9.30(1,bs), 8.90(1Hs), 8.50(2H,s&d), 8.45(1H,d), 8.20(1H,d), 7.40(5H,bm), 7.10(4H,2d), 6.80(1H,d).

Aufarbeitung

  1. customPrepared
  2. temperatureheated
  3. filtrationThe cooled solution was filtered through a plug of Celite®
  4. concentrationconcentrated
  5. customtriturated with iso-hexane (3×20 ml)
  6. customThe resultant solid was purified via flash column chromatography on silica gel
  7. washeluting with 5% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-52983b87950a43cda84d08387891d5a9
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727256B1

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