Cesium carbonate → 5-(3-Chloropyridin-4-yl)-6-(3-fluorophenyl)pyrazin-2-amine

HRID 1710692

Reaktionsgleichung

Br[C:2]1[N:3]=[CH:4][C:5]([NH2:15])=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1.[Cl:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[Cl:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:2]1[N:3]=[CH:4][C:5]([NH2:15])=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A microwave oven reactor was charged with 5-bromo-6-(3-fluorophenyl)pyrazin-2-amine (Preparation 1, 0.3 g, 1.11 mmol), (3-chloropyridin-4-yl)boronic acid (212 mg, 1.03 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloride dichloromethane complex (1:1) (39 mg, 0.047 mmol), dioxane (8 mL) and a 1.2M aqueous solution of cesium carbonate was added (1.9 mL, 2.39 mmol). The mixture was heated to 150° C. for 10 min in the microwave oven, then cooled, partitioned between water and ethyl acetate, the aqueous phase extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (dichloromethane to dichloromethane/methanol 90:10) furnished the title compound as a yellowish solid (78 mg, 39%).

Aufarbeitung

temperaturecooled
custompartitioned between water and ethyl acetate
extractionthe aqueous phase extracted twice with ethyl acetate
washthe organic layers washed with brine
dry with materialdried (MgSO4)
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-f00dfefcb4164b419097fc71b7024368
Quelldatensatz: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07790728B2

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