Potassium Phosphate, Tribasic → 4-Cyclopropyl-N-methylaniline

HRID 594797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594797
Br[C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.[CH:10]1(B(O)O)[CH2:12][CH2:11]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:10]1([C:2]2[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=2)[CH2:12][CH2:11]1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 2757052Benzenamine, 4-bromo-N-methyl-HCID 2760897Cyclopropylboronic acid

Produkt 1

HCID 153651924-Cyclopropyl-N-methylanilineAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension of 4-bromo-N-methylaniline (500 mg, 2.69 mmol), cyclopropylboronic acid (462 mg, 5.38 mmol), (cyclohexyl)3P+HBF4− (99 mg, 0.27 mmol) and K3PO4 (2.0 g, 9.4 mmol) in toluene (20 mL) and H2O (1 mL) was added Pd(OAc)2 (36 mg, 0.16 mmol) at r.t. under N2. The reaction was stirred at reflux overnight. The reaction was filtered, concentrated, and purified by silica gel chromatography (PE:EtOAc=10:1) to give 268 mg (68%) of the title compound as a brown oil. [M+H] Calc'd for C10H23N, 148. Found, 148.

Aufarbeitung

  1. temperatureat reflux overnight
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (PE:EtOAc=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-aa045eb2745248ef8d9fb592f067d491
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242968B2

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