Sodium Carbonate → 2-Methyl-7-(2,4,6-trimethyl-phenyl)-2H-indazole

HRID 1350536

반응식

HRID 1350536 반응식
Br[C:2]1[C:10]2[C:6](=[CH:7][N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[C:14]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.CCOC(C)=O>[CH3:11][N:8]1[CH:7]=[C:6]2[C:10]([C:2]([C:14]3[C:15]([CH3:20])=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=3[CH3:12])=[CH:3][CH:4]=[CH:5]2)=[N:9]1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 210945807-bromo-2-methyl-2H-indazole

생성물 1

HCID 210945602-Methyl-7-(2,4,6-trimethyl-phenyl)-2H-indazole수율 53%

시약·촉매·용매 3

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

7-Bromo-2-methyl-2H-indazole (4; 0.35 g, 1.66 mMol) and Pd(PPh3)4(0) (58 mg, 0.05 mMol) were stirred in 6 mL DME under argon for 30 min. 2,4,6-Trimethylbenzeneboronic acid (0.54 g, 3.3 mMol) was added, immediately followed by a solution of sodium carbonate (0.62 g, 5.8 mMol) in 5 mL water. The mixture was heated at a gentle reflux for 20 hr, then cooled to rt and diluted with EtOAc (75 mL). The mixture was then washed with brine and dried over MgSO4. Evaporation of the solvent afforded a light yellow solid which was flash chromatography on silica and eluted with hexane:EtOAc (9:1) which afforded 4b as a off-white solid 0.21 g (53%).

후처리

  1. temperatureThe mixture was heated at
  2. temperaturea gentle reflux for 20 hr
  3. washThe mixture was then washed with brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent
  6. customafforded a light yellow solid which
  7. washeluted with hexane:EtOAc (9:1) which

출처 및 근거

ORD 기록
ord-0fcc7831f0a144c0af8b1a414e49b5e5
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214699B2

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