Triacetoxyperiodinane → 3-((7-(4-chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)-6-(trifluoromethyl)picolinaldehyde

HRID 2101342ノート

反応式

HRID 2101342 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:30])[N:15]([CH2:17][C:18]4[C:19]([CH2:28][OH:29])=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=4)[N:16]=[C:10]3[C:9]=2[C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:30])[N:15]([CH2:17][C:18]4[C:19]([CH:28]=[O:29])=[N:20][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:23]=4)[N:16]=[C:10]3[C:9]=2[C:31]2[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 160048747-(4-chlorophenyl)-2-((2-(hydroxymethyl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

生成物 1

HCID 160048763-((7-(4-chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)-6-(trifluoromethyl)picolinaldehyde収率 99%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The title compound was also prepared as follows: To a stirring solution of 7-(4-chlorophenyl)-2-((2-(hydroxymethyl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (162.4 mg, 0.32 mmol) in CH2Cl2 (5 mL) at room temperature was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane, 201 mg, 0.48 mmol) in one portion. The resulting mixture was stirred at room temperature for 10 min, then quenched by addition of water. The aqueous layer was extracted with CH2Cl2 (10 mL×2). The combined CH2Cl2 layers were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was purified using a silica gel cartridge (12 g) eluted with a gradient of ethyl acetate (30-100%) in hexanes to obtain 160 mg (99%) of the title compound as a yellow foam. HPLC/MS: retention time=2.78 min, [M+H]+=510.6.

後処理

  1. customquenched by addition of water
  2. extractionThe aqueous layer was extracted with CH2Cl2 (10 mL×2)
  3. washThe combined CH2Cl2 layers were washed with saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe product was purified
  8. washeluted with a gradient of ethyl acetate (30-100%) in hexanes

出典と根拠

ORDレコード
ord-dbc1aeadd79342c99f16201677b15953
出典データセット
uspto-grants-2009_08
特許番号
US07572808B2

反応ノート

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