Potassium Phosphate, Tribasic → HCID 89784259, Verbindung

HRID 1056296Notizen

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([C:7]([NH2:9])=[O:8])[NH:5][CH:6]=1.[C:10]([NH:14][C:15]1[C:24]([CH3:25])=[N:23][C:22]2[C:17](=[C:18](B3OC(C)(C)C(C)(C)O3)[CH:19]=[CH:20][CH:21]=2)[N:16]=1)([CH3:13])([CH3:12])[CH3:11].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.O>[C:10]([NH:14][C:15]1[C:24]([CH3:25])=[N:23][C:22]2[C:17]([N:16]=1)=[C:18]([C:2]1[CH:3]=[C:4]([C:7]([NH2:9])=[O:8])[NH:5][CH:6]=1)[CH:19]=[CH:20][CH:21]=2)([CH3:13])([CH3:12])[CH3:11]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 4-bromo-1H-pyrrole-2-carboxamide (100 mg, 0.529 mmol), N-(tert-butyl)-3-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxalin-2-amine (174b; 311 mg, 0.529 mmol), K3PO4 (337 mg, 1.587 mmol), XPhos (Strem Chemicals, Inc.; 25.2 mg, 0.053 mmol), and (Aldrich; 24.22 mg, 0.026 mmol) in a mixture of dioxane (4.0 mL) and water (1.0 mL) was stirred under argon at 100° C. for 16.5 h. The reaction mixture was then concentrated onto silica gel and chromatographically purified (silica gel, 0-100% EtOAc/hexanes) to provide 4-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-2-carboxamide (86.7 mg, 0.268 mmol, 51% yield) as a light-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (1H, br. s.), 7.78 (1H, dd, J=2.6, 1.5 Hz), 7.61 (1H, dd, J=7.3, 1.3 Hz), 7.54 (1H, dd, J=8.1, 1.5 Hz), 7.44 (1H, br. s.), 7.31 (1H, t, J=7.7 Hz), 7.22-7.26 (1H, m), 6.94 (1H, br. s.), 5.78 (1H, s), 2.53 (3H, s), 1.53 (9H, s). m/z (ESI, +ve) 324.0 (M+H)+.

Aufarbeitung

concentrationThe reaction mixture was then concentrated onto silica gel
customchromatographically purified (silica gel, 0-100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-81b66f1c99e44ab6846405836e03f674
Quelldatensatz: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09394297B2

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