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Water → 3-Methyl-2-(2-methylphenyl)pyridine

HRID 1836320
Notes
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Reaction equation

HRID 1836320 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]1([CH3:18])[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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>[CH3:8][C:7]1[C:2]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH3:18])=[N:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2208322-Bromo-3-methylpyridineHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 144731913-Methyl-2-(2-methylphenyl)pyridine

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-bromo-3-methylpyridine (1.09 g; 6.34 mmol), o-tolylboronic acid (1.29 g; 9.50 mmol), and Pd(PPh3)4 (147 mg; 2 mol %) in DME (30 ml) is stirred for 10 minutes at room temperature. Sodium carbonate (32 ml of 1M solution in water; 32 mmol) is added to this mixture and the mixture is heated for 16 hours at 80° C. The reaction mixture is treated with water and extracted with dichloromethane. The combined extracts are washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue is purified by flash chromatography over silica gel (elution with 20% EtOAc/Hexane) to 3-methyl-2-o-tolyl-pyridine as a yellow oil. 1H NMR(300 MHz, CDCl3) δ 8.51(d, 1H), 7.58(d, 1H), 7.27-7.15(m, 5H), 2.14(s, 3H), 2.10(s, 3H).

Workup

  1. temperaturethe mixture is heated for 16 hours at 80° C
  2. extractionextracted with dichloromethane
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography over silica gel (elution with 20% EtOAc/Hexane) to 3-methyl-2-o-tolyl-pyridine as a yellow oil

Sources & evidence

ORD record
ord-d630fb59616641958cb134ced6404e5e
Source dataset
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06777422B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes