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

HRID 1350536Notes

Reaction equation

HRID 1350536 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-0fcc7831f0a144c0af8b1a414e49b5e5
Source dataset
uspto-grants-2007_05
Patent number
US07214699B2

Reaction notes

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