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5-[(4-Chloro-2-fluorophenyl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione → Ethyl 3-(4-chloro-2-fluorophenyl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

HRID 561396
ノート
印刷プレビュー

反応式

HRID 561396 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[C:27]3[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH:9]2C(=O)O[C:12](C)([CH3:16])[O:11][C:10]2=[O:18])=[C:4]([F:31])[CH:3]=1>N1C=CC=CC=1.C(O)C.[Cu]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[C:27]3[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:9][C:10]([O:11][CH2:12][CH3:16])=[O:18])=[C:4]([F:31])[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

HCID 583924735-[(4-Chloro-2-fluorophenyl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

生成物 1

HCID 58392210Ethyl 3-(4-chloro-2-fluorophenyl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 702Ethanol溶媒HCID 1049Pyridine溶媒

実験手順

5.0 mg (0.08 mmol) of copper powder were added to 3.60 g (7.79 mmol) of the compound from Example 15A in 56 ml of pyridine and 14 ml of ethanol. The reaction mixture was heated under reflux for 1 h. It was concentrated, and the residue was taken up in ethyl acetate, washed with 1N hydrochloric acid, dried over magnesium sulfate, filtered through silica gel and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 2.23 g (70% of theory) of the title compound.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. concentrationIt was concentrated
  4. washwashed with 1N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through silica gel
  7. concentrationconcentrated
  8. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

出典と根拠

ORDレコード
ord-e3826bbd62f94ade872cf169e19c37d7
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08063234B2

反応ノート

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