1-Pyrrolidineethanamine → 5-Bromo-N-[2-(pyrrolidin-1-yl)ethyl]pyridin-2-amine

HRID 1916589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916589
C([O-])([O-])=O.[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:54]1[CH:59]=[CH:58][C:57]([Br:60])=[CH:56][N:55]=1.[NH2:61][CH2:62][CH2:63][N:64]1[CH2:68][CH2:67][CH2:66][CH2:65]1>C1(C)C=CC=CC=1.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:60][C:57]1[CH:58]=[CH:59][C:54]([NH:61][CH2:62][CH2:63][N:64]2[CH2:68][CH2:67][CH2:66][CH2:65]2)=[N:55][CH:56]=1

Komponenten

9

Edukt 4

HCID 13441-PyrrolidineethanamineHCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 634876Binap, (A+-)-

Produkt 1

HCID 626427485-Bromo-N-[2-(pyrrolidin-1-yl)ethyl]pyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

13.8 g (100.0 mmol) K2CO3, 79 mg (0.12 mmol) 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and 28 mg (0.12 mmol) Pd(OAc)2 are added successively to a solution of 1.5 g (6.33 mmol) 2,5-dibromopyridine and 0.98 mL (7.60 mmol) 1-(2-aminoethyl)-pyrrolidine in 60 mL toluene. The reaction is refluxed for 40 h. The solvent is eliminated i.vac. and the residue is taken up in 150 mL EtOAc and 100 mL water. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Purification is carried out by column chromatography on silica gel (gradient: EtOAc/MeOH/NH3 19:1:0.1 to EtOAc/MeOH/NH3 9:1:0.1).

Aufarbeitung

  1. temperatureThe reaction is refluxed for 40 h
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-7129f45d21e24b6fb1a6b29c9ffb5bd5
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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