Potassium Carbonate → Ethyl 3-(5-(2-formyl-3,5-bis(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405185

Reaktionsgleichung

Br[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[C:3]=1[CH:4]=[O:5].CC1(C)C(C)(C)OB([C:26]2[CH:27]=[CH:28][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:33])=[N:30][CH:31]=2)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:4]([C:3]1[C:6]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:2]=1[C:26]1[CH:27]=[CH:28][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:33])=[N:30][CH:31]=1)=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

2-bromo-4,6-bis(trifluoromethyl)benzaldehyde (100 mg, 0.31 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (119 mg, 0.34 mmol), Pd(dppf)Cl2 (23 mg, 0.03 mmol), and 2M K2CO3 (0.31 mL, 0.62 mmol), were dissolved in 1,4-dioxane (1.0 mL) and heated to 100° C. After 70 min the resulting mixture was cooled to room temperature, diluted with DCM, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Aufarbeitung

temperatureAfter 70 min the resulting mixture was cooled to room temperature
dry with materialdried (Na2SO4)
concentrationconcentrated
custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-bf921c0c8e4e4efc98e1e80d12b92bc1
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08748624B2

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