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

HRID 1350536

反応式

HRID 1350536 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0fcc7831f0a144c0af8b1a414e49b5e5
出典データセット
uspto-grants-2007_05
特許番号
US07214699B2

関連ノート

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