2-Aminopyridine → HCID 58545059, compound

HRID 404149Notes

Reaction equation

HRID 404149 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.CC(C)([O-])C.[K+]>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]>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:3][CH:4]=1

Participants

7

Reactant 3

HCID 104392-AminopyridineHCID 5642162-Bromo-5-methylpyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 58545059HCID 58545059, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

2-Bromo-5-methylpyridine (300 mg, 1.74 mmol), 2-aminopyridine (180 mg, 1.91 mmol), potassium tert-butoxide (293 mg, 2.61 mmol), (±)-BINAP (4.3 mg, 0.07 mmol) and Pd2(dba)3 (4 mg, 0.05 mmol) were stirred in toluene (4 mL) at 90° C. under Ar(g). After 17 h stirring, the reaction was diluted with CH2Cl2 (5 mL), and silica was added. The solvent was removed under reduced pressure and the resulting dry loaded material purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:2) to furnish I as a yellow solid (187 mg, 58%).

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting dry
  4. custompurified by silica gel column chromatography
  5. washeluting with CH2Cl2/MeOH (100:2)

Sources & evidence

ORD record
ord-353d08d6d5b94de380826db59aa77b5f
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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