Sodium Carbonate → N-(3-morpholin-4-yl-quinoxalin-6-yl)-2-phenyl-isobutyramide

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Reaktionsgleichung

Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:9]2)=[CH:4][CH:3]=1.[C:18]1([C:24]([CH3:44])([CH3:43])[C:25]([NH:27]C2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.CCO>[N:12]1([C:8]2[CH:7]=[N:6][C:5]3[C:10]([N:9]=2)=[CH:11][C:2]([NH:27][C:25](=[O:26])[C:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH3:44])[CH3:43])=[CH:3][CH:4]=3)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 7-bromo-2-morpholin-4-yl-quinoxaline [intermediate example 2.1] (50 mg), 2-phenyl-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-isobutyramide (87 mg, 0.24 mmol) and Pd(PPh3)4 in 1:1 Toluene/EtOH (2 mL) was treated with 1M aq. sodium carbonate solution and heated at 120° C. under microwave irradiation for 15 minutes. The reaction was partitioned between EtOAc and water, the phases separated and the organic layer concentrated in vacuo. The reaction was repeated and the combined crude products were purified by trituration with DMSO to give the title compound (108 mg). UPLC-MS: RT=1.36 min; m/z (ES+) 453.27 [MH+]; required MW=452.56.

Aufarbeitung

customThe reaction was partitioned between EtOAc and water
customthe phases separated
concentrationthe organic layer concentrated in vacuo
customthe combined crude products were purified by trituration with DMSO

Quellen und Nachweise

ORD-Eintrag: ord-d0d57fc8a0b141bc9eefbe50462d506e
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09340528B2

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