Water → HCID 67976364、化合物

HRID 706654ノート

反応式

HRID 706654 の反応式
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH3:23])[N:16]=2)[N:3]=1.[C:24](=O)([O-])[O-].[K+].[K+].CB(O)O.O>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:22]([O:21][C:17]1[N:16]=[C:15]([CH2:14][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([CH3:24])=[N:3]2)[CH:20]=[CH:19][CH:18]=1)[CH3:23]

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 67976141HCID 67976141、化合物

生成物 1

HCID 67976364HCID 67976364、化合物収率 28.4%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 3-bromo-1-((6-ethoxypyridin-2-yl)methyl)-4-nitro-1H-indazole (0.500 g, 1.33 mmol) in dioxane (0.2M, 7 mL) was treated with potassium carbonate (0.916 g, 6.63 mmol), methylboronic acid (0.793 g, 13.3 mmol), water (0.239 mL, 13.3 mmol), followed by tetrakis(triphenylphosphine)palladium (0) (0.0766 g, 0.0663 mmol) at ambient temperature, purging under argon. The mixture was refluxed overnight, cooled to ambient temperature, filtered through glass fiber filter paper, concentrated and purified on silica (10-75% EtOAc in hexanes) to give 1-((6-ethoxypyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole (0.118 g, 28% yield).

後処理

  1. custompurging under argon
  2. temperatureThe mixture was refluxed overnight
  3. filtrationfiltered through glass fiber
  4. filtrationfilter paper
  5. concentrationconcentrated
  6. custompurified on silica (10-75% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-9616e6f1db3c4e36afa2181bb6452d4e
出典データセット
uspto-grants-2015_11
特許番号
US09174981B2

反応ノート

読み込み中…