Water → 2-(2,6-Dimethyl-phenyl)4-methyl-5-nitro-pyridine

HRID 602544Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1B(O)O.Cl[C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=1.C([O-])([O-])=O.[Na+].[Na+].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.CCO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2,6-dimethylphenylboronic acid (6.5 g, 43.5 mmol), 2-chloro-4-methyl-5-nitro-pyridine (5 g, 28.9 mmol), Pd(PPh3)4, (1.5 g, 1.5 mmol), Na2CO3 (4.6 g, 43.5 mm water (20 mL), and EtOH (5 mL) is heated in a sealed tube under nitrogen at 110° C. for 18 hours. The mixture is cooled to room temperature, diluted with EtOAc (150 mL), washed with saturated solution of Na2CO3 (50 mL 3×), water (50 mL) and brine (50 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue is purified by chromatography on silica gel (Hexane/EtOAc, 6:1) to afford 2-(2,6-dimethyl-phenyl)-4-methyl-5-nitro-pyridine as a colorless oil.

Workup

temperatureThe mixture is cooled to room temperature
washwashed with saturated solution of Na2CO3 (50 mL 3×), water (50 mL) and brine (50 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe residue is purified by chromatography on silica gel (Hexane/EtOAc, 6:1)

Sources & evidence

ORD record: ord-8405865ab2ca428dac4aa38ec0ba3e14
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906528B2

Reaction notes

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