2-Aminopyridine → HCID 58545047, compound

HRID 404145Notes

Reaction equation

HRID 404145 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-eefe3b60957b496498680742c0b38771
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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