Sodium Carbonate → HCID 131733128, Verbindung

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Reaktionsgleichung

Br[C:2]1[S:6][C:5]([NH:7][C:8]([C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])=[O:9])=[N:4][CH:3]=1.[CH3:18][C:19]1[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][C:22]2[N:23]=[CH:24]S[C:21]=2[CH:20]=1.C(=O)([O-])[O-:38].[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>[F:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([F:16])[C:10]=1[C:8]([NH:7][C:5]1[S:6][C:2]([C:27]2[C:19]([CH3:18])=[CH:20][C:21]3[O:38][CH:24]=[N:23][C:22]=3[CH:26]=2)=[CH:3][N:4]=1)=[O:9]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of N-(5-bromo(1,3-thiazol-2-yl))(2,6-difluorophenyl)carboxamide (31 mg, 0.1 mmol), 6-methyl-5-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))benzothiazole (14) (27 mg, 0.1 mmol), tetrakis(triphenylphosphine)-palladium(0) (Pd(Ph3P)4, 12 mg) and sodium carbonate (32 mg) in 0.5 ml DME, 0.5 ml EtOH and 0.2 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 purification to give 4.6 mg (2,6-difluorophenyl)-N-[5-(6-methylbenzoxazol-5-yl)(1,3-thiazol-2-yl)]carboxamide (50) as pale brown solid (yield: 11.9%; purity>90%). LC-MS: calcd. for C18H11F2N3OS2: 388 (M+1).

Aufarbeitung

concentrationphase was concentrated
customHPLC purification

Quellen und Nachweise

ORD-Eintrag: ord-b9800115d294414abf85515cd89d55b6
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09079891B2

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