Cesium carbonate → HCID 66834335, Verbindung

HRID 61834

Reaktionsgleichung

Br[C:2]1[C:22]([O:23][CH2:24][C@H:25]2[CH2:29][O:28][C:27]([CH3:31])([CH3:30])[O:26]2)=[CH:21][C:5]2[C:6]([CH3:20])([CH3:19])[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[C:16](=[O:17])[C:4]=2[CH:3]=1)=[CH:13][CH:12]=[C:11]([Cl:18])[CH:10]=4.C(=O)([O-])[O-:33].[Cs+].[Cs+].C1(P(C2CCCCC2)[C:45]2C=CC=C[C:46]=2[C:51]2[C:56](C(C)C)=CC(C(C)C)=C[C:52]=2C(C)C)CCCCC1>[Pd](Cl)Cl.C(#N)C.C(#N)C.C(#N)C>[Cl:18][C:11]1[CH:10]=[C:9]2[C:14]([C:15]3[C:16](=[O:17])[C:4]4[CH:3]=[C:2]([C:45]#[C:46][C:51]([OH:33])([CH3:56])[CH3:52])[C:22]([O:23][CH2:24][C@H:25]5[CH2:29][O:28][C:27]([CH3:31])([CH3:30])[O:26]5)=[CH:21][C:5]=4[C:6]([CH3:20])([CH3:19])[C:7]=3[NH:8]2)=[CH:13][CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To the mixture of 9-bromo-3-chloro-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound S7-1, 50 mg, 0.1 mmol), bis(acetonitrile) palladium (II) dichloride (2.6 mg, 0.01 eq.), cesium carbonate (195 mg, 6 eq.) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (14.3 mg, 0.03 eq.), acetonitrile (2 mL) was added and stirred at 80° C. for 12 hr. Tar-like residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain 3-chloro-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-9-(3-hydroxy-3-methyl-but-1-ynyl)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (brown powder, 105 mg).

Aufarbeitung

additionwas added
customTar-like residues obtained
concentrationafter concentration under reduced pressure
customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag: ord-a341512e166441b0aa8eb12b11989046
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09440922B2

Verknüpfte Notizen

Wird geladen…