Potassium Carbonate → HCID 89499550, Verbindung

HRID 333672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333672
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([O:14][CH3:15])=[N:4][C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[CH3:24][Si:25]([C:28]#[C:29][B-](F)(F)F)([CH3:27])[CH3:26].[K+].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C>[CH3:15][O:14][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)[C:2]([C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24])=[C:3]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:4]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 23673582PotassiuM (2-triMethylsilyl)ethynyltrifluoroborateHCID 53379588HCID 53379588, Verbindung2×

Produkt 1

HCID 89499550HCID 89499550, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of the compound 4-bromo-1,7-dimethoxy-3-(4-methoxyphenyl)isoquinoline (compound 26) (187 mg, 0.5 mmol), potassium (trimethylsilyl)ethynyltrifluoroborate (133 mg, 0.65 mmol), palladium diacetate (3.5 mg, 0.015 mmol), RuPhos (14 mg, 0.03 mmol) and potassium carbonate (318 mg, 1.5 mmol) dissolved in 2 mL of a distilled THF/degassed H2O mixture (10/1) is refluxed under argon for 2 hours. The reaction medium is filtered on silica then condensed under vacuum. The crude is purified on a silica column (cyclohexane/dichloromethane, 7/3). 182 mg (93%) of the 1,7-dimethoxy-3-(4-methoxyphenyl)-4-((trimethylsilyl)ethynyl)isoquinoline intermediate is obtained in the form of a brown solid which is used directly in the following stage,

Aufarbeitung

  1. customdegassed H2O mixture (10/1)
  2. temperatureis refluxed under argon for 2 hours
  3. filtrationThe reaction medium is filtered on silica
  4. customcondensed under vacuum
  5. customThe crude is purified on a silica column (cyclohexane/dichloromethane, 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-564cf0f97e8542a087471acfd4caaa68
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883763B2

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