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

HRID 1916589Notes

Reaction equation

HRID 1916589 reaction equation
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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-7129f45d21e24b6fb1a6b29c9ffb5bd5
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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