Triethylamine → Dimethyl 5,5'-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate

HRID 1042937

Reaktionsgleichung

Reaktionsgleichung von HRID 1042937
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:12])=[O:9])=[CH:4][C:3]=1I.[C:30]([C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][CH:38]=1)[NH2:35])#[CH:31].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O.[Cu]I>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:12])=[O:9])=[CH:4][C:3]=1[C:31]#[C:30][C:32]1[CH:38]=[CH:37][CH:36]=[C:34]([NH2:35])[CH:33]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 86668544dimethyl 5,5'-{N-[(6-amino-5-iodopridin-3-yl)carbonyl]sulfonimidoyl}dipentanoate

Produkt 1

HCID 86668543Dimethyl 5,5'-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To the degassed mixture of dimethyl 5,5′-{N-[(6-amino-5-iodopridin-3-yl)carbonyl]sulfonimidoyl}dipentanoate (1.16 g, 2.15 mmol, 1.0 equiv.), 3-ethynylaniline (0.34 mL, 3.25 mmol, 1.5 equiv.), and triethylamine (1.2 mL, 8.61 mmol, 4.0 equiv.) in anhydrous DMF (7 mL) under nitrogen atmosphere was added CuI (81.5 mg, 0.42 mmol, 0.2 equiv.) and PdCl2(Ph3P)2 (150.6 mg, 0.21 mmol, 0.1 equiv.). The reaction mixture was stirred at room temperature for 15 minutes. The reaction was then diluted with EtOAc, washed with sat. aq. NaHCO3, aq. NH4Cl, and brine, and lastly dried with anhydrous Na2SO4. The solution was decanted, concentrated, and the oily residue was subject to a gradient column chromatography (from EtOAc-Hex 1:3 to neat EtOAc) to give the title compound as a white foam (1.0 g).

Aufarbeitung

  1. washwashed with sat. aq. NaHCO3, aq. NH4Cl, and brine
  2. dry with materiallastly dried with anhydrous Na2SO4
  3. customThe solution was decanted
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ea7c59af467f4bc2bc2f2bdd9482a475
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08558002B2

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