Triethylamine → (S)-3-{[5-({[methyl(oxo)phenyl-lambda6-sulfanylidene]amino}carbonyl)pyridin-3-yl]ethynyl}benzoic acid

HRID 391523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391523
[CH3:1][S@:2](=[O:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([C:11]#[C:12][Si](C)(C)C)[CH:8]=[N:7][CH:6]=1.I[C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29]([OH:31])=[O:30].C(N(CC)CC)C.[H][H].N#N.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C.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.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][S@:2](=[N:3][C:4]([C:5]1[CH:10]=[C:9]([C:11]#[C:12][C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29]([OH:31])=[O:30])[CH:8]=[N:7][CH:6]=1)=[O:17])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

10

Edukt 5

HCID 8471TriethylamineHCID 120603-Iodobenzoic acidHCID 2724141Tetrabutylammonium FluorideHCID 24953135(S)-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamideHCID 178514468HCID 178514468, Verbindung

Produkt 1

HCID 24953841(S)-3-{[5-({[methyl(oxo)phenyl-lambda6-sulfanylidene]amino}carbonyl)pyridin-3-yl]ethynyl}benzoic acidAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11776TriphenylphosphineKatalysatorHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of (S)—N-[methyl(oxo)phenyl-λ6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide (54 mg, 0.15 mmol), 3-iodobenzoic acid (56 mg, 0.23 mmol), dichlorobis(triphenylphosphine)palladium(II) (11 mg, 0.02 mmol), triphenylphosphine (1.0 mg, 0.004 mmol) and triethylamine (0.073 mL, 0.53 mmol) in 1.5 mL DMF at room temperature was degassed using vacuum and a H2/N2 (1:1) mixture and then copper(I) iodide (2 mg, 0.01 mmol) added. The reaction was heated to 60° C. then tetrabutylammonium fluoride (1.0 M in THF, 0.15 ml) added over 3.5 minutes. After 25 minutes the reaction was partitioned between EtOAc and dilute AcOH. The EtOAc layer was collected and washed with H2O, brine, dried with anhydrous Na2SO4 and concentrated to a yellow solid. The solid was triturated with EtOAc at room temperature to give the title compound as a yellow solid (45 mg, 74%).

Aufarbeitung

  1. customwas degassed
  2. customAfter 25 minutes the reaction was partitioned between EtOAc and dilute AcOH
  3. customThe EtOAc layer was collected
  4. washwashed with H2O, brine
  5. dry with materialdried with anhydrous Na2SO4
  6. concentrationconcentrated to a yellow solid
  7. customThe solid was triturated with EtOAc at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-fd50c8e91d9548be97608481a512e9c6
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383825B2

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