Sodium Carbonate → 2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol

HRID 58630

Reaktionsgleichung

[Cl:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5](I)=[C:6]([CH:8]=1)[NH2:7].[CH2:11]([Si:13]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:14]#[C:15][CH2:16][CH2:17][OH:18])[CH3:12].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[Cl:1][C:2]1[CH:8]=[C:6]2[C:5]([C:15]([CH2:16][CH2:17][OH:18])=[C:14]([Si:13]([CH2:19][CH3:20])([CH2:21][CH3:22])[CH2:11][CH3:12])[NH:7]2)=[CH:4][C:3]=1[CH3:10]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

5-chloro-2-iodo-4-methylaniline (1.50 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (2.36 mL; 11.22 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.229 g; 0.280 mmol), lithium chloride (0.237 g; 5.61 mmol) and sodium carbonate (1.19 g; 11.22 mmol) were suspended in DMF (14 mL) and the mixture was stirred at 100° C. for 15 hours. The mixture was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulphate, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 1.44 g (79%) of the title compound as a brown oil.

Aufarbeitung

concentrationThe mixture was concentrated under reduced pressure
additiondiluted in ethyl acetate
washThe organic layer was successively washed with brine, sodium thiosulphate
customdried
concentrationconcentrated under reduced pressure
customThe crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag: ord-cf662b2f82ea4046ac3dbaf33facd596
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09434722B2

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