Nitrogen → N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-4-methyl-3-[(trimethylsilyl)ethynyl]benzamide

HRID 1527885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527885
[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23](I)[CH:22]=3)=[CH:15][C:14]=2[C:30]([F:33])([F:32])[F:31])[CH2:8][CH2:7]1)([CH3:4])=[O:3].N#N.C(N(CC)C(C)C)(C)C.[CH3:45][Si:46]([C:49]#[CH:50])([CH3:48])[CH3:47]>[Cu]I.CCOC(C)=O.O.CN(C=O)C>[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([C:50]#[C:49][Si:46]([CH3:48])([CH3:47])[CH3:45])[CH:22]=3)=[CH:15][C:14]=2[C:30]([F:33])([F:32])[F:31])[CH2:8][CH2:7]1)([CH3:4])=[O:3]

Komponenten

9

Edukt 4

HCID 947NitrogenHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 68911921N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide

Produkt 1

HCID 68911889N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-4-methyl-3-[(trimethylsilyl)ethynyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide (5 mmol), Pd[(PPh3)]4 (289 mg, 0.25 mmol), CuI (71 mg, 0.375 mmol) is placed in a schlenk flask. The flask is subjected to 3 cycles of vacuum-refilling with N2. To this mixture is added anhydrous N,N-diisopropylethylamine (1.1 mL, 6 mmol), DMF (5 mL), and trimethylsilylacetylene (0.92 mL, 6.5 mmol). This solution is stirred at rt for 24 h. Water and EtOAc are added to the reaction mixture to facilitate the extraction. The combined organic layers are dried over Na2SO4, filtered, and then concentrated on a rotavap and the crude product is purified on a silica gel column (eluent: 5% MeOH in CH2Cl2, MeON is pre-saturated with ammonia gas).

Aufarbeitung

  1. extractionthe extraction
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated on a rotavap
  5. customthe crude product is purified on a silica gel column (eluent: 5% MeOH in CH2Cl2, MeON is pre-saturated with ammonia gas)

Quellen und Nachweise

ORD-Eintrag
ord-3df43deea04240a399e6c0476dbef169
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090561B2

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