Diisopropylethylamine → 3-(4-Pyrrolidin-1-ylmethylphenyl)propynoic acid-(4-prop-1-ynylphenyl)amide

HRID 734992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734992
C(N(C(C)C)C(C)C)C.I[C:11]1[CH:22]=[CH:21][C:14]([CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:13][CH:12]=1.[C:23]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:36])[C:34]#[CH:35])=[CH:28][CH:27]=1)#[C:24][CH3:25]>[Cu]I>[C:23]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:36])[C:34]#[C:35][C:11]2[CH:22]=[CH:21][C:14]([CH2:15][N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:13][CH:12]=2)=[CH:28][CH:27]=1)#[C:24][CH3:25]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 185258671-(4-Iodobenzyl)pyrrolidineHCID 86060737Propynoic acid-(4-prop-1-ynylphenyl)amide2×

Produkt 1

HCID 578456773-(4-Pyrrolidin-1-ylmethylphenyl)propynoic acid-(4-prop-1-ynylphenyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator

Versuchsvorschrift

10 mL of acetonitrile is degassed and combined with 0.35 mL (2 mmol) of ethyldiisopropylamine and 0.2 g (0.69 mmol) of 1-(4-iodobenzyl)pyrrolidine. Then the mixture is again degassed and 13 mg of copper (I) iodide, 34 mg of tetrakistriphenylphosphine palladium, and 137 mg (0.75 mmol) of propynoic acid-(4-prop-1-ynylphenyl)amide are then added in succession. The reaction mixture is stirred for 24 hours at ambient temperature and then combined with 60 mg of propynoic acid-(4-prop-1-ynylphenyl)amide. After 24 hours, the mixture is evaporated down. The purification is carried out by column chromatography on silica gel (dichloromethane/methanol/ammonia (30:1:0.1 to 20:1:0.1)). Yield: 24 mg (10% of theory); C23H22N2O (M=342.44); calc.: molecular ion peak (M+H)+: 343; found: molecular ion peak (M+H)+: 343; Rf value: 0.2 (silica gel, dichloromethane/methanol/ammonia=10:1:0.1).

Aufarbeitung

  1. custom10 mL of acetonitrile is degassed
  2. customThen the mixture is again degassed
  3. waitAfter 24 hours
  4. customthe mixture is evaporated down
  5. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-2692bdccfee544e8be4fc5cd1cb82eff
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592373B2

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