Sodium Carbonate → HCID 86699396, Verbindung

HRID 1777564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1777564
[F:1][C:2]1[C:3](I)=[C:4]([CH:6]=[C:7]([F:10])[C:8]=1[F:9])[NH2:5].[F:12][C:13]1[CH:14]=[C:15]([CH:37]=[CH:38][CH:39]=1)[CH2:16][C:17]1[CH:36]=[CH:35][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]#[C:27][Si:28]([CH2:33][CH3:34])([CH2:31][CH3:32])[CH2:29][CH3:30])=[O:22])=[CH:19][CH:18]=1.[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>[F:12][C:13]1[CH:14]=[C:15]([CH:37]=[CH:38][CH:39]=1)[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]2[C:3]3[C:4](=[CH:6][C:7]([F:10])=[C:8]([F:9])[C:2]=3[F:1])[NH:5][C:27]=2[Si:28]([CH2:29][CH3:30])([CH2:31][CH3:32])[CH2:33][CH3:34])=[O:22])=[CH:35][CH:36]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 18541883HCID 18541883, VerbindungHCID 67974550HCID 67974550, Verbindung

Produkt 1

HCID 86699396HCID 86699396, VerbindungAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3,4,5-Trifluoro-2-iodoaniline (0.100 g; 0.366 mmol), 4-(3-fluorobenzyl)-N-(4-(triethylsilyl)but-3-ynyl)benzamide (0.145 g; 0.366 mmol), bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.015 g; 0.018 mmol), lithium chloride (0.015 mg; 0.366 mmol) and sodium carbonate (0.078 g; 0.732 mmol) were suspended in DMF (5 mL) and the mixture was stirred at 100° C. for 72 hours. The solution was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 60% ethyl acetate in heptane) to afford 0.057 g (29%) of the title compound.

Aufarbeitung

  1. concentrationThe solution was concentrated under reduced pressure
  2. additiondiluted in ethyl acetate
  3. washThe organic layer was successively washed with brine, sodium thiosulfate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 60% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-278fa5355e19465c995d4300161e1a13
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266832B2

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