Sodium Carbonate → 3-(2-Methylphenyl)-4-pyridinecarboxylic acid

HRID 1975959

Reaktionsgleichung

I[C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[C:17]1([CH3:26])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O>C(COC)OC.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:17]1([CH3:26])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a suspension of 1.05 g (4.21 mmol) 3-iodo-isonicotinic acid in 15 ml dimethoxyethane were added successively 0.243 g tetrakis(triphenylphosphine)palladium(0), 4.2 ml 2 M sodium carbonate solution in water and 0.69 g (5.05 mmol) o-tolylboronic acid. The mixture was heated under argon at 80° C. for 18 h. After cooling to room temperature the phases were separated and the organic phase was washed twice with water (pH=9). The combined aqueous layers were than adjusted to pH=3 and extracted with five portions ethyl acetate. The combined organic layers were washed with brine, dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 0.68 g (75%) of the title compound as pale yellow crystals.

Aufarbeitung

temperatureAfter cooling to room temperature the phases
customwere separated
washthe organic phase was washed twice with water (pH=9)
extractionextracted with five portions ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried (magnesium sulfate)
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-235b2a2d7eb04c3789284bd5fa903a25
Quelldatensatz: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06225316B1

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