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Sodium Carbonate → 7-(4-Methoxy-2-methyl-phenyl)-2-methyl-2H-indazole

HRID 1350538
Notes
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Reaction equation

HRID 1350538 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][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[C:16]([CH3:23])[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[C:10]3[C:6](=[CH:7][N:8]([CH3:11])[N:9]=3)[CH:5]=[CH:4][CH:3]=2)=[C:16]([CH3:23])[CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2773486(4-Methoxy-2-methylphenyl)boronic acidHCID 210945807-bromo-2-methyl-2H-indazole

Product 1

HCID 210946097-(4-Methoxy-2-methyl-phenyl)-2-methyl-2H-indazoleYield 91%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

7-Bromo-2-methyl-2H-indazole (4; 1.76 g, 8.3 mMol) and tetrakis(triphenylphosphine)palladium(0) (0.28 g, 0.25 mMol) were stirred in 15 mL of DME under argon atmosphere for 30 min. 4-Methoxy-2-methylbenzeneboronic acid (1.52 g, 9.2 mMol) was added, immediately followed by a solution of sodium carbonate (3.1 g, 29.1 mMol) in 10 mL water. The mixture was heated at a gentle reflux for 4 hr, and then cooled to rt and diluted with EtOAc (150 mL). The organic phase was washed with brine and dried over magnesium sulfate. Evaporation of the solvent afforded an oil, which was flash chromatographed on SiO2 and eluted with hexane:EtOAc (9:1) to afford 4c (1.9 g; 91%).

Workup

  1. temperatureThe mixture was heated at
  2. temperaturea gentle reflux for 4 hr
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customafforded an oil, which
  7. customchromatographed on SiO2
  8. washeluted with hexane:EtOAc (9:1)

Sources & evidence

ORD record
ord-7be26b18d67f4c43b88e305200aa304a
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07214699B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes