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Diazomethane → 6-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)cyclopropyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one

HRID 77488
ノート
印刷プレビュー

反応式

HRID 77488 の反応式
[F:1][CH:2]([F:38])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[N:25]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:24](=[O:37])[CH:23]=[CH:22]4)=[CH:13][N:12]=2)=[CH:6][CH:5]=1.[N+](=[CH2:41])=[N-]>C(OCC)C>[F:38][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[CH:15][C:14]([CH:17]3[CH2:41][CH:18]3[C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[N:25]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:24](=[O:37])[CH:23]=[CH:22]4)=[CH:13][N:12]=2)=[CH:6][CH:5]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 9550DiazomethaneHCID 86679781(E)-6-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one

生成物 1

HCID 866797806-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)cyclopropyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one収率 49%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
-10 °C

実験手順

To a stirred solution of (E)-6-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one (0.15 g, 0.280 mmol) in diethyl ether (10 mL) was added PdOAc2 (6.28 mg, 0.028 mmol). The reaction mixture was cooled to −10° C., and a cold solution of diazomethane in ether (generated from aqueous KOH (0.45 g) and NMU (0.6 g) at −15° C.) was added. The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was filtered through celite, diluted with diethyl ether, and washed with water and saturated NaCl solution. The organic layer was dried over sodium sulfate, concentrated, and purified by flash chromatography on silica gel column using 15% ethyl acetate in hexane to give 6-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)cyclopropyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one as a yellow gum (0.075 g, 49%). LCMS: RT 2.317 min, (M+H) 551.

後処理

  1. filtrationThe reaction mixture was filtered through celite
  2. additiondiluted with diethyl ether
  3. washwashed with water and saturated NaCl solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel column

出典と根拠

ORDレコード
ord-04418496064546c3b4e228744ccee340
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841301B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート