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Potassium Phosphate, Tribasic → 4-cyclopropyl-N-(3-(dimethylamino)propyl)-N-methyl-2-nitrobenzenamine

HRID 1042695
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1042695
C1(B2O[C:7]([CH3:10])([CH3:9])[C:6]([CH3:12])([CH3:11])O2)CC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].BrC1C=[CH:26][C:25]([N:28]([CH3:35])[CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])=[C:24]([N+:36]([O-:38])=[O:37])C=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1.O>[CH:6]1([C:7]2[CH:9]=[CH:26][C:25]([N:28]([CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])[CH3:35])=[C:24]([N+:36]([O-:38])=[O:37])[CH:10]=2)[CH2:11][CH2:12]1
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Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 16109013HCID 16109013, Verbindung

Produkt 1

HCID 161090144-cyclopropyl-N-(3-(dimethylamino)propyl)-N-methyl-2-nitrobenzenamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a pressure vessel was added 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (900 mg, 5.36 mmol), potassium phosphate (3.0 g, 14.42 mmol), and 0.82 mL water. After stirring at RT for 15 minutes, N-(4-Bromo-2-nitro-phenyl)-N,N′,N′-trimethyl-propane-1,3-diamine (Step 1, 1.30 g, 4.12 mmol), palladium acetate (92 mg, 0.412 mmol), tricyclohexylphosphine (231 mg 0.824 mmol), and 21 ml toluene were added. The reaction was sealed and stirred at 80° C. for 19 h. The reaction was then cooled to RT, quenched with EtOAc and extracted into water, washed once with brine, and then dried over Mg2SO4. The crude mixture was then purified by reverse phase chromatography to yield the title compound as a dark red-brown oil. MS (M+H−)=278; Calc'd for C15H23N3O2=277.36.

Aufarbeitung

  1. customThe reaction was sealed
  2. stirringstirred at 80° C. for 19 h
  3. temperatureThe reaction was then cooled to RT
  4. customquenched with EtOAc
  5. extractionextracted into water
  6. washwashed once with brine
  7. dry with materialdried over Mg2SO4
  8. customThe crude mixture was then purified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-55b5b722ee9e46148069d7b9797f82f0
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08557996B2

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