Tolylboronic acid → 3-Methyl-2-(4-methylphenyl)pyridine

HRID 2262382Notes

Reaction equation

HRID 2262382 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=1>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 79799Tolylboronic acidHCID 2208322-Bromo-3-methylpyridine

Product 1

HCID 30175113-Methyl-2-(4-methylphenyl)pyridineYield 75.4%

Procedure

4-methylphenylboronic acid (20.0 g, 0.147 mol) was reacted with 2-bromo-3-methylpyridine (21.1 g, 0.123 mol) under standard Suzuki coupling condition. A small amount of unreacted 2-bromo-3-methylpyridine was removed via vacuum distillation. Purification via flash silica gel chromatography with a 1/99 to 7.5/92.5 EtOAc/hexane solvent gradient yielded 17.0 g of 2-(4-methylphenyl)-3-methylpyridine as a colorless liquid.

Workup

  1. customA small amount of unreacted 2-bromo-3-methylpyridine was removed via vacuum distillation
  2. customPurification via flash silica gel chromatography with a 1/99 to 7.5/92.5 EtOAc/hexane solvent

Sources & evidence

ORD record
ord-4c94e05a13734f0ea5472c86a45753e3
Source dataset
uspto-grants-2010_12
Patent number
US07851072B2

Reaction notes

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