Potassium Phosphate, Tribasic → N-[5-(5-chloro-2-methybenzoxazol-6-yl)(1,3-thiazol-2-yl)](2-chlorophenyl)carboxamide

HRID 1524237Notizen

Reaktionsgleichung

Br[C:2]1[S:6][C:5]([NH:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[O:9])=[N:4][CH:3]=1.[Cl:17][C:18]1[C:19](B2OC(C)(C)C(C)(C)O2)=[CH:20][C:21]2[O:25][C:24]([CH3:26])=[N:23][C:22]=2[CH:27]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC(=O)OCC.[Cl-].[Na+].O>CN(C=O)C.O>[Cl:17][C:18]1[C:19]([C:2]2[S:6][C:5]([NH:7][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])=[O:9])=[N:4][CH:3]=2)=[CH:20][C:21]2[O:25][C:24]([CH3:26])=[N:23][C:22]=2[CH:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A mixture of N-(5-bromo(1,3-thiazol-2-yl))(2-chlorophenyl)carboxamide (47, 25 mg, 0.08 mmol), 2-(5-chloro-2-methylbenzoxzzol-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4) (29 mg, 0.1 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane complex (1:1) (12 mg) and potassium phosphate (21 mg) in 1 ml DMF and 0.2 ml water was heated under Ar in microwave reactor at 150° 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 3.1 mg N-[5-(5-chloro-2-methybenzoxazol-6-yl)(1,3-thiazol-2-yl)](2-chlorophenyl)carboxamide (49) as pale brown solid (yield: 9.6%; purity>90%). LC-MS: calcd. for C18H11Cl2N3O2S: 405 (M+1).

Aufarbeitung

concentrationphase was concentrated
customHPLC purification

Quellen und Nachweise

ORD-Eintrag: ord-0ffbb3331dc0440ca5826062e13340b8
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09079891B2

Notizen zur Reaktion

Wird geladen…