2-Aminopyridine → HCID 58545058, compound

HRID 404147

Reaction equation

HRID 404147 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=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]>[C:8]1([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 104392-AminopyridineHCID 1047002-Bromo-4-phenylpyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 58545058HCID 58545058, compoundYield 62.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

2-Bromo-4-phenylpyridine (280 mg, 1.19 mmol), 2-aminopyridine (124 mg, 1.31 mmol), potassium tert-butoxide (201 mg, 1.79 mmol), (±)-BINAP (3 mg, 0.05 mmol) and Pd2(dba)3 (2.7 mg, 0.03 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 (100:2), to furnish I as a yellow solid (183 mg, 62%).

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-12d4c056b99b495e824f039e45e5457c
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Linked notes

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