2-Aminopyridine → HCID 14934442, compound

HRID 244512Notes

Reaction equation

HRID 244512 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].Br[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][N:10]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:10][CH:11]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 104392-AminopyridineHCID 782402-Bromo-5-nitropyridineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 23676156Sodium t-butoxide

Product 1

HCID 14934442HCID 14934442, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of pyridin-2-amine, 9, (0.5 g; 2.5 mmol), 2-bromo-5-nitropyridine, 10, (0.28 g; 2.9 mmol), 1,3-Bis(diphenylphosphino)propane (0.04 g; 0.08 mmol) in toluene was added to a mixture of sodium tert butoxide (0.33 g; 3.5 mmol) and Pd(dba)3 (0.05 g; 0.05 mmol) in toluene and allowed to stir at ambient temperature for 18 hours. The mixture was filtered through a bed of celite and the solvent removed under reduced pressure. The crude mixture was purified on a flash silica gel column (hexane/ethyl acetate) to afford 5-nitro-N-(pyridin-2-yl)pyridin-2-amine, 11, (0.25 g; 47%).

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. customthe solvent removed under reduced pressure
  3. customThe crude mixture was purified on a flash silica gel column (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6121a443820641e9a9912b5f6aeff5cf
Source dataset
uspto-grants-2014_02
Patent number
US08658650B2

Reaction notes

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