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

HRID 734992ノート

反応式

HRID 734992 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2692bdccfee544e8be4fc5cd1cb82eff
出典データセット
uspto-grants-2009_09
特許番号
US07592373B2

反応ノート

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