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Phthalimide → 2-((5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methyl)-1H-isoindole-1,3(2H)-dione

HRID 709615
ノート
印刷プレビュー

反応式

HRID 709615 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:21]O)=[N:14][C:15]=1[O:16][CH2:17][CH:18]([CH3:20])[CH3:19].[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:21][N:27]2[C:23](=[O:33])[C:24]3[C:25](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:26]2=[O:28])=[N:14][C:15]=1[O:16][CH2:17][CH:18]([CH3:19])[CH3:20]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 117760235(5-(2-Fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methanol

生成物 1

HCID 1177602692-((5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methyl)-1H-isoindole-1,3(2H)-dione収率 90.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 1140Toluene溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methanol (177 mg) in THF (5.0 mL) was added phthalimide (102 mg), triphenylphosphine (181 mg) and a 40% solution of diethyl azodicarboxylate in toluene (320 μL), and the mixture was stirred at room temperature for 15 hr. Water was added, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (228 mg) as a colorless oil.

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-b637d5188f3d4999b8554ece85100b58
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181186B2

反応ノート

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