2-Aminopyridine → HCID 58545047, compound

HRID 523901Notes

Reaction equation

HRID 523901 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[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:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 104392-AminopyridineHCID 27340872-Bromo-4-methylpyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 58545047HCID 58545047, compoundYield 77.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

2-Bromo-4-methylpyridine (0.195 mL, 1.74 mmol), 2-aminopyridine (180 mg, 1.91 mmol), potassium tert-butoxide (293 mg, 2.61 mmol), (±)-BINAP (4.3 mg, 6.96 mmol) and Pd2(dba)3 (4 mg, 4.35 mmol) were stirred in toluene (2.5 mL) at 90° C. under Ar(g). After 17 h stirring, the reaction mixture was diluted with CH2Cl2 (2.5 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 (100:1 to 100:2) to furnish I as a yellow solid (249 mg, 77%).

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 (100:1 to 100:2)

Sources & evidence

ORD record
ord-387a158915a64a21a58237352378ab2d
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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