Water → 2-Amino-3-nitro-5-pyridin-3-yl-pyridine

HRID 722071Notes

Reaction equation

HRID 722071 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20](Br)=[CH:19][N:18]=1.O>O1CCOCC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl>[NH2:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:19][N:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 1388782-Amino-5-bromo-3-nitropyridineHCID 27343783-Pyridinylboronic acid

Product 1

HCID 218827122-Amino-3-nitro-5-pyridin-3-yl-pyridine

Reagents, catalysts & solvents 2

HCID 11050900Dichlorobis(tricyclohexylphosphine)pallium (II)CatalystHCID 312751,4-DioxaneSolvent

Procedure

0.21 g of dichlorobis(tricyclohexylphosphine)palladium, 0.66 g of 3-pyridyl-boronic acid and 14 ml of a 2N sodium carbonate solution are added to a solution of 1.02 g of 2-amino-5-bromo-3-nitropyridine in 40 ml of degassed dioxane. The mixture is heated to reflux under N2 for 28 hours and, after cooling and addition of water, extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate, concentrated and the residue is crystallized from ethyl acetate. This gives 0.58 g of the title compound of m.p. 226–228° C. The mass spectrum shows the molecular peak MH+ at 217.2 Da.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux under N2 for 28 hours
  3. temperatureafter cooling
  4. extractionextracted three times with dichloromethane
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-a9fbc260b4fa49dfacc3a3a1be196a4f
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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