Triethylamine → dimethyl 5,5'-[N-({6-amino-5-[(4-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate

HRID 1042941

Reaktionsgleichung

Reaktionsgleichung von HRID 1042941
[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:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)#[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][C:35]([NH2:36])=[CH:34][CH:33]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 37600254-EthynylanilineHCID 86668544dimethyl 5,5'-{N-[(6-amino-5-iodopridin-3-yl)carbonyl]sulfonimidoyl}dipentanoate

Produkt 1

HCID 86668546dimethyl 5,5'-[N-({6-amino-5-[(4-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoateAusbeute 95,9 %

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-iodopyridin-3-yl)carbonyl]sulfonimidoyl}dipentanoate (234 mg, 0.434 mmol, 1.0 equiv.), 4-ethynylaniline (76.3 mg, 0.651 mmol, 1.5 equiv.), and triethylamine (0.242 mL, 1.736 mmol, 4.0 equiv.) in anhydrous DMF (2 mL) under nitrogen atmosphere was added CuI (16.5 mg, 0.087 mmol, 0.2 equiv.) and PdCl2(Ph3P)2 (30.5 mg, 0.043 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 EtOAc) yielding dimethyl 5,5′-[N-({6-amino-5-[(4-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate as brown oil (220 mg).

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-d0347535fe854422b39a96941067f802
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08558002B2

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