Potassium Phosphate, Tribasic → 6-(3-(tert-butylamino)-2-methyl-quinoxalin-5-yl)-1H-pyrrolo[1,2-c]imidazol-3(2H)-one

HRID 1056298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056298
Br[C:2]1[CH:3]=[C:4]2[CH2:8][NH:7][C:6](=[O:9])[N:5]2[CH:10]=1.[C:11]([NH:15][C:16]1[C:25]([CH3:26])=[N:24][C:23]2[C:18](=[C:19](B3OC(C)(C)C(C)(C)O3)[CH:20]=[CH:21][CH:22]=2)[N:17]=1)([CH3:14])([CH3:13])[CH3:12].[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.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:11]([NH:15][C:16]1[C:25]([CH3:26])=[N:24][C:23]2[C:18]([N:17]=1)=[C:19]([C:2]1[CH:3]=[C:4]3[CH2:8][NH:7][C:6](=[O:9])[N:5]3[CH:10]=1)[CH:20]=[CH:21][CH:22]=2)([CH3:14])([CH3:13])[CH3:12]

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 89783758N-(tert-butyl)-3-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxalin-2-amineHCID 897938476-Bromo-1,2-dihydro-3H-pyrrolo[1,2-c]imidazol-3-one

Produkt 1

HCID 897938486-(3-(tert-butylamino)-2-methyl-quinoxalin-5-yl)-1H-pyrrolo[1,2-c]imidazol-3(2H)-oneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 6-bromo-1H-pyrrolo[1,2-c]imidazol-3(2H)-one (20.5 mg, 0.102 mmol), N-(tert-butyl)-3-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxalin-2-amine (Example 174b; 43.5 mg, 0.102 mmol), K3PO4 (64.9 mg, 0.306 mmol), Pd2dba3 (Aldrich; 4.67 mg, 5.10 μmol), and XPhos (Strem Chemicals, Inc. MA; 4.86 mg, 10.20 μmol) in a mixture of dioxane (1.0 mL) and water (0.25 mL) was stirred under argon at 70° C. for 70 min. The reaction mixture was subsequently concentrated onto silica gel and chromatographically purified (silica gel, 0-100% EtOAc/hexanes) to provide 6-(3-(tert-butylamino)-2-methyl-quinoxalin-5-yl)-1H-pyrrolo[1,2-c]imidazol-3(2H)-one (19.0 mg, 0.057 mmol, 56% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.94 (1H, s), 7.79 (1H, br. s.), 7.70 (1H, d, J=7.4 Hz), 7.37 (1H, t, J=7.8 Hz), 6.56 (1H, d, J=1.2 Hz), 5.41 (1H, br. s.), 4.71 (1H, br. s.), 4.50 (2H, s), 2.57 (3H, s), 1.59 (9H, s). m/z (ESI, +ve) 336.0 (M+H)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-60a1dceea3bb48229c4432b525ee8ef0
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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