Dichloromethane → methyl 4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline-6-carboxylate

HRID 8246

Reaktionsgleichung

Reaktionsgleichung von HRID 8246
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[CH2:6](Cl)Cl.BrC1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[C:13]2[C:20]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[N:23][N:22]2[CH2:31][CH2:32][CH2:33][C:21]=12.[C]=O>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:6][O:3][C:1]([C:2]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[C:13]2[C:20]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[N:23][N:22]2[CH2:31][CH2:32][CH2:33][C:21]=12)=[O:4]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 101350276-bromo-4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolineHCID 178418416HCID 178418416, Verbindung

Produkt 1

HCID 10133736methyl 4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of sodium acetate (0.84 g, 10.2 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II):CH2Cl2 (42 mg, 0.05 mmol) in methanol (40 mL) is added 6-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (1.0 g, 2.56 mmol). The mixture is heated at 90° C. under 68 psi carbon monoxide for 24 h. The mixture is cooled, filtered, and concentrated in vacuo. The product is partitioned between ethyl acetate and: water. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on SiO2 (dichloromethane to 2% methanol/dichloromethane) to yield a solid, 918 mg (97%).

Aufarbeitung

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe product is partitioned between ethyl acetate
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on SiO2 (dichloromethane to 2% methanol/dichloromethane)
  8. customto yield a solid, 918 mg (97%)

Quellen und Nachweise

ORD-Eintrag
ord-8a78da593f264a14928d76c76ca79538
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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