Triethylborane → HCID 9970412, Verbindung

HRID 1824804Notizen

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=3Br)[S:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(B(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=3)[S:9][C:5]=2[CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 6-methoxy-2-(2-bromo-3-methoxy-phenyl)-benzothiazole (0.182, 0.52 mmol) in dry DMF (3 mL) was added cesium carbonate (0.51 g, 1.57 mmol), triethylborane (0.58 mL, 1M in THF, 0.58 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride dichloromethane (18 mg, 0.022 mmol). The mixture was heated to 50° C. for 24 h, then cooled to room temperature. Saturated sodium bicarbonate was added and the mixture was extracted with ethylacetate. Combined ethylacetate were washed with brine, concentrated. After chromatographic purification gave 6-methoxy-2-(3-methoxy-phenyl)-benzothiazole (54 mg, 38% yield) as a white solid. Mass spec: MH+=272.

Aufarbeitung

temperaturecooled to room temperature
extractionthe mixture was extracted with ethylacetate
washCombined ethylacetate were washed with brine
concentrationconcentrated
customAfter chromatographic purification

Quellen und Nachweise

ORD-Eintrag: ord-028ee8b0118f4ab2b5262db55e64423a
Quelldatensatz: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07045539B2

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