2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 2-(3-(tert-butylamino)-2-ethylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

HRID 1056177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056177
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]([CH2:17][CH3:18])=[N:7]2.CC1(C)C(C)(C)OB([C:27]2[NH:35][C:34]3[CH2:33][CH2:32][NH:31][C:30](=[O:36])[C:29]=3[CH:28]=2)O1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CO.C(Cl)Cl>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:13]([NH:12][C:9]1[C:8]([CH2:17][CH3:18])=[N:7][C:6]2[C:11]([N:10]=1)=[C:2]([C:27]1[NH:35][C:34]3[CH2:33][CH2:32][NH:31][C:30](=[O:36])[C:29]=3[CH:28]=1)[CH:3]=[CH:4][CH:5]=2)([CH3:16])([CH3:15])[CH3:14]

Komponenten

8

Edukt 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 21226129Dichloromethane methanolHCID 897834962-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-C]pyridin-4-oneHCID 897847628-bromo-N-(tert-butyl)-3-ethylquinoxalin-2-amine

Produkt 1

HCID 897839392-(3-(tert-butylamino)-2-ethylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneAusbeute 4,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 8-bromo-N-(tert-butyl)-3-ethylquinoxalin-2-amine (312b; 134.8 mg, 0.437 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (609) (345 mg, 0.90 mmol), K2PO4 (279 mg, 1.31 mmol), X-Phos (Strem Chemicals, Inc.) (20 mg, 0.04 mmol), and Pd2dba3 (Aldrich, 20 mg, 0.022 mmol) in a mixture of 1,4-dioxane (5.0 mL) and water (1.00 mL) was stirred under argon at 100° C. for 1 h. The reaction mixture was then concentrated onto silica gel and chromatographically purified (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) to provide 2-(3-(tert-butylamino)-2-ethylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (6.7 mg, 0.018 mmol, 4% yield) as a yellow-orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.00 (1H, br. s.), 7.82 (1H, dd, J=7.4, 1.2 Hz), 7.60 (1H, dd, J=8.1, 1.3 Hz), 7.33 (1H, t, J=7.8 Hz), 7.02 (1H, d, J=2.0 Hz), 6.96 (1H, br. s.), 6.04 (1H, s), 3.42 (2H, td, J=6.9, 2.2 Hz), 2.90 (2H, q, J=7.2 Hz), 2.85 (2H, t, J=7.0 Hz), 1.56 (9H, s), 1.29 (3H, t, J=7.2 Hz). m/z (ESI, +ve) 364.1 (M+H)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-70ddd2b475354a16bb051df499078116
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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