Potassium Carbonate → 4-Chloro-2-phenylpyridin-3-amine

HRID 1401121Notes

Reaction equation

HRID 1401121 reaction equation
[CH:1]1[C:6]([Cl:7])=[C:5]([NH2:8])[C:4](Cl)=[N:3][CH:2]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:8][C:5]1[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:3][CH:2]=[CH:1][C:6]=1[Cl:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 98555622,4-Dichloropyridin-3-amine

Product 1

HCID 578565174-Chloro-2-phenylpyridin-3-amine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

3-Amino-2-4-dichloropyridine d (0.7047 g, 4.32 mmol), phenylboronic acid (0.5177 g, 4.24 mmol), K2CO3 (0.8023 g, 5.80 mmol), and Pd(PPh3)4 (0.0702 g, 0.0607 mmol) were combined. The sample was evacuated and purged with nitrogen three times. Dry DMF (2 mL) and deoxygenated H2O (0.4 mL) were added. The sample was microwaved at 130° C. for 40 minutes. The reaction mixture was diluted with H2O (50 mL) and extracted with EtOAc (3×50 mL). The EtOAc extracts was dried over MgSO4 and filtered. The crude material was adsorbed onto silica gel and purified by flash chromatography (40 g SiO2, 0-30% EtOAc in hexanes) to give 3-amino-4-chloro-2-phenylpyridine e (0.435 g, 2.12 mmol, 49%).

Workup

  1. customThe sample was evacuated
  2. custompurged with nitrogen three times
  3. customDry DMF (2 mL) and deoxygenated H2O (0.4 mL)
  4. additionwere added
  5. customThe sample was microwaved at 130° C. for 40 minutes
  6. additionThe reaction mixture was diluted with H2O (50 mL)
  7. extractionextracted with EtOAc (3×50 mL)
  8. dry with materialThe EtOAc extracts was dried over MgSO4
  9. filtrationfiltered
  10. custompurified by flash chromatography (40 g SiO2, 0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4be8ea3a917345b2afc204cbb7cdf12d
Source dataset
uspto-grants-2014_12
Patent number
US08907092B2

Reaction notes

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