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Sodium Carbonate → Benzyl 1-(cyclopropylmethyl)-2-oxo-5-phenyl-1,2-dihydropyridin-3-ylcarbamate

HRID 1725633
ノート
印刷プレビュー

反応式

HRID 1725633 の反応式
[CH:1]1([CH2:4][N:5]2[CH:10]=[C:9](I)[CH:8]=[C:7]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]2=[O:23])[CH2:3][CH2:2]1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1([CH2:4][N:5]2[CH:10]=[C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:8]=[C:7]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]2=[O:23])[CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 68958794Benzyl 1-(cyclopropylmethyl)-5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamate

生成物 1

HCID 68808625Benzyl 1-(cyclopropylmethyl)-2-oxo-5-phenyl-1,2-dihydropyridin-3-ylcarbamate

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒
HCID 702Ethanol溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

Tetrakis(triphenylphosphine)palladium(0) (0.132 mg, 0.11 mmol) and benzyl 1-(cyclopropylmethyl)-5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamate (0.097 mg, 0.229 mmol) in tetrahydrofuran (1 mL) were stirred at room temperature for 30 minutes. A solution of phenylboronic acid in ethanol (1 mL) was then added to the reaction mixture. After 1 h, a 2 M solution of sodium carbonate (1 mL) was added and the reaction was heated to reflux. After 3 h, the mixture was allowed to cool to ambient temperature and extracted with ethyl acetate and water. The combined organic extracts were washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by chromatography (silica gel, 5% to 30% ethyl acetate in hexanes gradient elution) gave the title compound (0.061 g). MS 375 (M+1)

後処理

  1. temperaturethe reaction was heated to reflux
  2. waitAfter 3 h
  3. extractionextracted with ethyl acetate and water
  4. washThe combined organic extracts were washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification
  9. washby chromatography (silica gel, 5% to 30% ethyl acetate in hexanes gradient elution)

出典と根拠

ORDレコード
ord-63a86a18a19f4222807b602aa9b7d28f
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07491713B2

反応ノート

読み込み中…

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