2-Bromopyridine → N-(Pyridin-3-yl)pyridin-2-amine

HRID 404174Notes

Reaction equation

HRID 404174 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.C(O[K])(C)(C)C>C1(C)C=CC=CC=1.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]>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:10]=1

Participants

7

Reactant 3

HCID 79732-BromopyridineHCID 100093-AminopyridineHCID 178418922HCID 178418922, compound

Product 1

HCID 12140009N-(Pyridin-3-yl)pyridin-2-amineYield 90%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

2-Bromopyridine (0.3 mL, 3.16 mmol), 3-aminopyridine (327 mg, 3.48 mmol), tBuOK (532 mg, 4.74 mmol), (±)-BINAP (79 mg, 0.126 mmol) and Pd2(dba)3 (72 mg, 0.079 mmol) were stirred in toluene (5 mL) at 90° C. under Ar(g) for 19 h. The reaction mixture was then diluted with CH2Cl2 (5 mL) and silica was added followed by the removal of the solvent under reduced pressure. The resulting dry loaded material was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:3 to 100:6) to furnish I as a brown oil (483 mg, 90%).

Workup

  1. additionwas added
  2. customfollowed by the removal of the solvent under reduced pressure
  3. customThe resulting dry
  4. customwas purified by silica gel column chromatography
  5. washeluting with CH2Cl2/MeOH (100:3 to 100:6)

Sources & evidence

ORD record
ord-bfde0e3c017e47c3a674ffff79f9a07d
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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