Sodium Carbonate → HCID 60198794, Verbindung

HRID 76382

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

Under an argon atmosphere, to 4 ml 1,2-dimethoxyethane are added 5-bromo-pyridine-2-carboxylic acid (93 mg, 0.46 mmol), 4-(2-carboxyethyl)benzeneboronic acid (106 mg, 0.55 mmol), 0.51 ml of a 2M aqueous sodium carbonate solution and dichlorobis-(triphenylphosphin) palladium (II) (20 mg, 0.03 mmol). The mixture is stirred at 90° C. overnight, cooled and quenched with water. Ethyl acetate is added and the mixture adjusted to pH=2 with 1M hydrochloric acid. After threefold extraction with ethyl acetate, the combined organic layers are dried over magnesium sulfate, filtered, and evaporated in vacuo. The residue is purified by silica gel chromatography (eluent:dichloromethane/methanol 5:1).

Aufarbeitung

temperaturecooled
customquenched with water
additionEthyl acetate is added
extractionAfter threefold extraction with ethyl acetate
dry with materialthe combined organic layers are dried over magnesium sulfate
filtrationfiltered
customevaporated in vacuo
customThe residue is purified by silica gel chromatography (eluent:dichloromethane/methanol 5:1)

Quellen und Nachweise

ORD-Eintrag: ord-c62d31b447de42588a5de4dbc9c4fcc4
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08835637B2

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