Sodium Carbonate → N-(2-chlorophenyl)[5-(6-methylbenzothiazol-5-yl)(2-thienyl)]carboxamide

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Reaktionsgleichung

Br[C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[O:8])=[CH:4][CH:3]=1.[CH3:17][C:18]1[C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][C:21]2[N:22]=[CH:23][S:24][C:20]=2[CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(=O)OCC.[Cl-].[Na+].O>COCCOC.CCO.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:7]([C:5]1[S:6][C:2]([C:26]2[C:18]([CH3:17])=[CH:19][C:20]3[S:24][CH:23]=[N:22][C:21]=3[CH:25]=2)=[CH:3][CH:4]=1)=[O:8]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of (5-bromo(2-thienyl))-N-(2-chlorophenyl)carboxamide (7, 21 mg, 0.07 mmol), 6-methyl-5-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))benzothiazole (14) (19 mg, 0.07 mmol), tetrakis(triphenylphosphine)-palladium(0) (Pd(Ph3P)4, 8 mg) and sodium carbonate (22 mg) in 0.5 ml DME, 0.5 ml EtOH and 0.25 ml water was heated under Ar in microwave reactor at 110° C. for 30 min. The reaction mixture was worked up with EA/brine. Org. phase was concentrated and then subjected to prep HPLC chromatography to furnish 22.6 mg of N-(2-chlorophenyl)[5-(6-methylbenzothiazol-5-yl)(2-thienyl)]carboxamide (17) as yellow solid (yield: 83.9%; purity>95%). LC-MS: calcd. for C19H13ClN2OS2: 385 (M+1).

Aufarbeitung

concentrationphase was concentrated

Quellen und Nachweise

ORD-Eintrag: ord-44f42b8851304829a8c71204b4db7b5a
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09079891B2

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