Cesium carbonate → 6-Vinyl-1H-indole-3-carbaldehyde

HRID 1527163

Reaktionsgleichung

Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH:13]([B-](F)(F)F)=[CH2:14].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>Cl[Pd]Cl.O.C1COCC1>[CH:13]([C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1)=[CH2:14]

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

6-bromoindole-3-carboxaldehyde (5 g, 22.3 mmol), potassium vinyltrifluoroborate (4.48 g, 33.5 mmol), PdCl2 (396 mg, 2.23 mmol), PPh3 (1.75 mg, 6.7 mmol) and Cs2CO3 (2.18 mg, 66.9 mmol) were combined in a 500 mL flask placed under a nitrogen atmosphere. THF (135 mL) and H2O (15 mL) were added and the yellow solution was heated at 85° C. for 2 days. The reaction was allowed to cool to RT, water was added and the mixture was extracted twice with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1) to give the title compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.4; MS (LC/MS): 172.0 [M+H]+ 170.1 [M−H]−; tR (HPLC conditions a): 2.95 min.

Aufarbeitung

temperatureto cool to RT
extractionthe mixture was extracted twice with CH2Cl2
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag: ord-c12580fb42b24572b9f6d64137f543fa
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09085555B2

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