4-Aminopyridine → (S)-[3-(1-amino-ethyl)-phenyl]-pyridin-4-yl-amine

HRID 2183467Notes

Reaction equation

HRID 2183467 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)[CH3:9])(C)(C)C.[NH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C(Cl)Cl.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]>[NH2:7][C@H:8]([C:10]1[CH:11]=[C:12]([NH:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[CH:13]=[CH:14][CH:15]=1)[CH3:9]

Participants

7

Reactant 3

HCID 17274-AminopyridineHCID 62657Potassium Phosphate, TribasicHCID 56971804(S)-N-Boc-1-(3-bromophenyl)ethylamine

Product 1

HCID 60004117(S)-[3-(1-amino-ethyl)-phenyl]-pyridin-4-yl-amineYield 103.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (S)-[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (3 g), 4-aminopyridine (1.88 g), Pd2(dba)3 (915 mg), di-t-butylbiphenylphosphine (298 mg), K3PO4 (4.24 g) in DME (20 mL) was stirred under reflux for 24 h. The reaction mixture was cooled down to room temperature, diluted with methylene chloride, filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography using Biotage eluting with 5% MeOH in ethyl acetate to give the desired product (2.2 g) as a solid.

Workup

  1. temperatureunder reflux for 24 h
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by flash chromatography
  5. washeluting with 5% MeOH in ethyl acetate

Sources & evidence

ORD record
ord-73a443b1df5f4abd86a7984885efeef0
Source dataset
uspto-grants-2005_05
Patent number
US06900210B2

Reaction notes

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