2,6-Dichloropyridine → Pyridine, 2-chloro-6-(4-methylphenyl)-

HRID 2080802Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Cl[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[N:13]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.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>[Cl:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-Methylphenylboronic acid (1.00 g), 2,6-dichloropyridine (3.27 g), tetrakis(triphenylphosphine)palladium(0) (0.255 g) and potassium phosphate (3.12 g) were dissolved in toluene (35 ml) and water (6.0 ml). The mixture was stirred at 80° C. for 15 hours under a nitrogen atmosphere. The organic layer was separated, washed with a saturated aqueous sodium hydrogen carbonate solution, and dried with anhydrous magnesium sulfate and the solvent was distilled off. The resultant was crudely purified through silica gel column chromatography (chloroform), thereby obtaining a mixture (4.02 g) containing the subject compound.

Workup

customThe organic layer was separated
washwashed with a saturated aqueous sodium hydrogen carbonate solution
dry with materialdried with anhydrous magnesium sulfate
distillationthe solvent was distilled off
customThe resultant was crudely purified through silica gel column chromatography (chloroform)

Sources & evidence

ORD record: ord-768e2b33edf648e9bf07096e5607a5a8
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932281B2

Reaction notes

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