Sodium Carbonate → HCID 178418705, Verbindung

HRID 9337

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.C([O-])(=O)C.[K+].C([O:23][N:24]=[C:25]1[C:33]2([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:32]2[C:27](=[CH:28][CH:29]=[C:30](Br)[CH:31]=2)[NH:26]1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.Cl[Pd]Cl>[OH:23][N:24]=[C:25]1[C:33]2([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:4]3[CH:5]=[C:6]([CH:7]=[C:2]([F:1])[CH:3]=3)[C:8]#[N:9])[CH:31]=2)[NH:26]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 3-fluoro-5-cyano-bromobenzene (0.4 g, 2.0 mmol) in dry DMF (10 ml) was added diboron pinacolate ester (0.63 g, 2.5 mmol), potassium acetate (0.65 g, 6.7 mmol) and PdCl2 (dppf) (0.2 g) and the reaction was heated to 80° C. under a nitrogen atmosphere. After 8 h. from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (0.2 g, 0.5 mmol), PdCl2 (dppf) (0.05 g) and sodium carbonate (1.30 g, 12.5 mmol) were added and heating at 80° C. was continued. After 8 h., the reaction was cooled and partitioned between water and ethyl acetate, the organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20) to give the desired product (0.14 g, 0.33 mmol, 66%).

Aufarbeitung

temperatureheating at 80° C.
temperaturethe reaction was cooled
custompartitioned between water and ethyl acetate
washthe organic layer was washed with brine
dry with materialdried (MgSO4)
customevaporated
customThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20)

Quellen und Nachweise

ORD-Eintrag: ord-542e11faf0c04255953d092e54cc0035
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091234B2

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