Potassium Phosphate, Tribasic → Ethyl 3-(5-(2-formyl-6-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405179

Reaktionsgleichung

Cl[C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].CC1(C)C(C)(C)OB([C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([F:13])([F:12])[F:11])[C:2]=1[C:22]1[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=1)=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

2-Chloro-3-(trifluoromethyl)benzaldehyde (199 mg, 0.96 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (410 mg, 1.2 mmol), Pd2(dba)3 (26 mg, 0.03 mmol), and 2M K3PO4 (aq) (1.0 mL, 2.0 mmol) were dissolved in 1,4-dioxane (2.9 mL) and heated to 100° C. After 2.5 h the resulting mixture was concentrated, taken up in DCM and the aqueous layer was extracted with DCM. The combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Aufarbeitung

concentrationAfter 2.5 h the resulting mixture was concentrated
extractionthe aqueous layer was extracted with DCM
dry with materialThe combined organics were dried (Na2SO4)
concentrationconcentrated
custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-8a53009bc9bd46ebb13421016b776abf
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08748624B2

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