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

HRID 523930Notes

Reaction equation

HRID 523930 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-d5f3940d0ed74874954e3c2242e8b026
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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