Sodium Carbonate → 3-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

HRID 58635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58635
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1I.[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>[OH:18][CH2:17][CH2:16][C:15]1[C:3]2[C:2](=[CH:9][CH:8]=[C:5]([C:6]#[N:7])[CH:4]=2)[NH:1][C:14]=1[Si:13]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:11][CH3:12]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-olHCID 44163954-Amino-3-iodobenzonitrile

Produkt 1

HCID 668321333-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrileAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24290Palladium ChlorideKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-amino-3-iodobenzonitrile (1.65 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (1.57 mL; 7.44 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.276 g; 0.338 mmol), lithium chloride (0.287 g; 6.76 mmol), sodium carbonate (1.43 g; 13.52 mmol) in DMF (14 mL) was stirred at 100° C. for 15 hours. The solution was filtered through celite, diluted in ethyl acetate, washed with brine and sodium thiosulphate, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane) to yield 0.873 g (43%) of the title compound as a yellow solid.

Aufarbeitung

  1. filtrationThe solution was filtered through celite
  2. additiondiluted in ethyl acetate
  3. washwashed with brine and sodium thiosulphate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-852fc4767c60491383d952da2fa0d845
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434722B2

Notizen zur Reaktion

Wird geladen…