Trimethylsilylacetylene → 6-(4-Chloro-benzoyl)-1-cyclopropylmethyl-4-(3-trimethylsilanylethynyl-phenyl)-1H-quinolin-2-one

HRID 1597480ノート

反応式

HRID 1597480 の反応式
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH2:18][CH:19]2[CH2:21][CH2:20]2)[C:13](=[O:22])[CH:12]=[C:11]3[C:23]2[CH:28]=[CH:27][CH:26]=[C:25](I)[CH:24]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:32][Si:33]([C:36]#[CH:37])([CH3:35])[CH3:34]>CN(C=O)C.C(NCC)C.[Cu]I>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH2:18][CH:19]2[CH2:21][CH2:20]2)[C:13](=[O:22])[CH:12]=[C:11]3[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:37]#[C:36][Si:33]([CH3:35])([CH3:34])[CH3:32])[CH:24]=2)=[O:7])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 185164516-(4-Chloro-benzoyl)-1-cyclopropylmethyl4-(3-iodo-phenyl)-1H-quinolin-2-one

生成物 1

HCID 185164466-(4-Chloro-benzoyl)-1-cyclopropylmethyl-4-(3-trimethylsilanylethynyl-phenyl)-1H-quinolin-2-one収率 92%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 86589549DMF Diethylamine溶媒

実験手順

A solution of 6-(4chloro-benzoyl)-1-cyclopropylmethyl-4-(3-iodo-phenyl)-1H-quinolin-2-one (4.0 g, 7.41 mmol) in DMF/diethylamine (1:1, 80 mL) was treated with palladium (II) bis(triphenyl)phosphine chloride (0.26 9, 0.37 mmol), trimethylsilylacetylene (1.09 g, 11.1 mmol), and copper (I) iodide (0.21 g, 1.09 mmol). The reaction mixture was stirred at room temperature for 3 hours, concentrated in vacuo, poured into H2O (450 mL), and filtered to give a crude brown foam. Purification by flash column chromatography (silica, ether:petroleum ether 1:1) gave 6-(4-Chloro-benzoyl)-1-cyclopropylmethyl-4-(3-trimethylsilanylethynyl-phenyl)-1H-quinolin-2-one (3.47 g, 92%) as a yellow solid.

後処理

  1. concentrationconcentrated in vacuo
  2. additionpoured into H2O (450 mL)
  3. filtrationfiltered
  4. customto give a crude brown foam
  5. customPurification by flash column chromatography (silica, ether:petroleum ether 1:1)

出典と根拠

ORDレコード
ord-e5356679358f4b178053ebffa0a861bf
出典データセット
uspto-grants-2001_09
特許番号
US06294552B1

反応ノート

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