Water → HCID 67976364, 화합물

HRID 706654노트

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HRID 706654 반응식
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]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 67976141HCID 67976141, 화합물

생성물 1

HCID 67976364HCID 67976364, 화합물수율 28.4%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9616e6f1db3c4e36afa2181bb6452d4e
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174981B2

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