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

HRID 1524222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1524222
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.[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.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:17][C:18]1[C:19]([C:2]2[S:6][C:5]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])=[O:8])=[CH:4][CH:3]=2)=[CH:20][C:21]2[O:25][C:24]([CH3:26])=[N:23][C:22]=2[CH:27]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 35083965-bromo-N-(2-chlorophenyl)thiophene-2-carboxamideHCID 667787335-Chloro-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazoleHCID 131718255Brine ethyl acetate

Produkt 1

HCID 56847660[5-(5-chloro-2-methylbenzoxazol-6-yl)(2-thienyl)]-N-(2-chlorophenyl)carboxamideAusbeute 33,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of (5-bromo(2-thienyl))-N-(2-chlorophenyl)carboxamide (7) (25 mg, 0.08 mmol), 2-(5-chloro-2-methylbenzoxazol-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4) (23 mg, 0.08 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 0.25 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 silica gel flash column chromatography. The isolated crude product was re-purified on prep HPLC to furnish 10.7 mg of [5-(5-chloro-2-methylbenzoxazol-6-yl)(2-thienyl)]-N-(2-chlorophenyl)carboxamide (8) as white solid (yield: 33.1%; purity>95%). LC-MS: calcd. for C19H12Cl2N2O2S: 404 (M+1).

Aufarbeitung

  1. concentrationphase was concentrated
  2. customThe isolated crude product
  3. customwas re-purified on prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-71a236e0142f4537ab7bcaf566e61918
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079891B2

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