Hydrochloric Acid → HCID 89812805, Verbindung

HRID 1481153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1481153
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[O:4].C([Sn](CCCC)(CCCC)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)CCC.CCOC(C)=O.Cl>CN(C=O)C.[Cl-].[Na+].O.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>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:9]=2)=[O:4]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 607632TributylphenyltinHCID 89813103Methyl 7-bromo-4-hydroxyisoquinoline-3-carboxylate

Produkt 1

HCID 89812805HCID 89812805, VerbindungAusbeute 75,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 7-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (400 mg, 1.42 mmol), tributylphenyltin (0.6 mL, 1.70 mmol), and PdCl2(PPh3)2 (200 mg, 0.28 mmol) in DMF (14 mL) was heated at 120° C. for 2 h under N2 atmosphere. After cooling the mixture to r.t., brine (10 mL) and EtOAc (30 mL) were added. 1 M HCl was added with stirring until pH was ˜3. The aqueous layer was extracted with additional EtOAc, and the organic layers were combined, washed with water, and dried over MgSO4. After evaporating the solvent, the crude product was purified by column chromatography (0-40% EtOAc/hexanes) to give 300 mg of the title compound. 1H NMR (CDCl3, 200 MHz): δ ppm=11.7 (s, 1H), 8.87 (s, 1H), 8.46 (d, 1H, J=8.6 Hz), 8.15 (d, 1H, J=1.4 Hz), 8.04 (dd, 1H, J=8.6 Hz, 2.0 Hz), 7.65-7.80 (m, 2H), 7.40-7.60 (m, 3H), 4.12 (s, 3H).

Aufarbeitung

  1. temperatureAfter cooling the mixture to r.t.
  2. extractionThe aqueous layer was extracted with additional EtOAc
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customAfter evaporating the solvent
  6. customthe crude product was purified by column chromatography (0-40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-108816d123b24f489d36597439284049
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409892B2

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