Water → HCID 67152537, compound

HRID 602522Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH2:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH3:21])[C:15]=1B(O)O)[CH3:13].C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.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.C(O)C>[CH2:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH3:21])[C:15]=1[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1)[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-4-methyl-5-nitro-pyridine (5.0 g, 29.0 mmol), 2,6-diethylphenylboronic acid (7.7 g, 43.3 mmol), Pd(PPh3)4, (1.0 g, 0.9 mmol), Na2CO3 (9.1 g, 86.5 mmol) in a mixture of toluene (200 mL), water (43 mL) and ethanol (10 mL) is heated at 100° C. under nitrogen overnight. The mixture is cooled to room temperature, diluted with EtOAc, washed with water, 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-diethyl-phenyl)-4-methyl-5-nitro-pyridine as a colorless oil.

Workup

temperatureThe mixture is cooled to room temperature
washwashed with water
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-f67fc737bad4486aa7fe95b47d2d9e05
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906528B2

Reaction notes

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