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Cesium carbonate → (S)-1-(1-(oxiran-2-ylmethyl)-1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)-pyridin-2(1H)-one

HRID 2390448
ノート
印刷プレビュー

反応式

HRID 2390448 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=4)=[CH:12][C:11]3=[O:26])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:31][C@@H:32]1[O:34][CH2:33]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[O:34]1[CH2:33][C@@H:32]1[CH2:31][N:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=4)=[CH:12][C:11]3=[O:26])=[CH:7][CH:8]=2)[CH:3]=[N: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

6

反応物 3

HCID 10796Cesium carbonateHCID 14292098(R)-(-)-Glycidyl-4-nitrobenzenesulfonateHCID 576255401-(1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one

生成物 1

HCID 57625522(S)-1-(1-(oxiran-2-ylmethyl)-1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)-pyridin-2(1H)-one収率 55.3%

試薬・触媒・溶媒 2

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒

実験手順

A mixture of 1-(1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (750 mg, 2.11 mmol), (R)-(−)-glycidyl nosylate (657 mg, 2.53 mmol) and cesium carbonate (1.03 g, 3.17 mmol) in methyl sulfoxide (6 mL) was stirred at ambient temperature overnight. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure. Purification by column chromatography (silica gel, ethyl acetate) gave the title compound (480 mg, 55%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.09 (d, J=0.9 Hz, 1H), 7.76-7.72 (m, 5H), 7.65 (d, J=9.0 Hz, 1H), 7.52 (d, J=7.2 Hz, 1H), 7.47 (dd, J=9.0, 2.1 Hz, 1H), 6.92 (d, J=1.8 Hz, 1H), 6.53 (dd, J=6.9, 1.8 Hz, 1H), 4.79 (dd, J=15, 3.0 Hz, 1H), 4.48 (dd, J=15.3, 5.7 hz, 1H), 3.41-3.37 (m, 1H), 2.88 (app t, J=4.5 Hz, 1H), 2.60 (dd, J=4.5, 2.4 Hz, 1H).

後処理

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic extracts were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography (silica gel, ethyl acetate)

出典と根拠

ORDレコード
ord-c316d430c2b748789872edafe4445570
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08273770B2

反応ノート

読み込み中…

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