Potassium Carbonate → HCID 22263547, compound

HRID 2100293Notes

Reaction equation

HRID 2100293 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.BrNC(=O)CCC(N)=O.NC1C(Br)=CC(C)=CN=1.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.CS(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 153482-Amino-5-methylpyridineHCID 66827Phenylboronic AcidHCID 5193802-Amino-3-bromo-5-methylpyridineHCID 9834204N-Bromosuccinamide

Product 1

HCID 22263547HCID 22263547, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

2-amino-3-phenyl-5-methylpyridine was prepared as follows: 2-amino-5-picoline (10.8 g, 0.1 M) was dissolved in glacial acetic acid (200 ml), and N-bromosuccinamide (20 g, 0.11 M) was added. The reaction mixture was stirred at room temperature for 17 hours. The reaction mixture was poured onto ice/water and the solid removed by filtration. The filtrate was basified with solid sodium hydroxide, and the resulting precipitate was isolated by filtration (12.8 g). The product, 2-amino-3-bromo-5-methylpyridine (3.7 g, 20 mmol), was dissolved in anhydrous DMSO (100 ml) under an atmosphere of nitrogen. Phenylboronic acid (2.66 g, 22 mmol) was added, followed by the addition of potassium carbonate (9.66 g, 70 mmol) and bis(triphenylphosphine)-palladium(II) chloride (426 mg, 0.6 mmol). The reaction mixture was heated to 80° C. with stirring for 15 hours. The reaction was cooled, poured into ice/water, and the crude product was collected by filtration. The resultant material was treated with 1 M aqueous hydrochloric acid (200 ml), stirred for 10 minutes, and filtered to remove insoluble residues. The filtrate was basified with solid sodium hydroxide, and the resultant yellow precipitate was filtered and dried to provide the product, 2-amino-3-phenyl-5-methylpyridine, as a pale yellow solid (2.25 g).

Workup

  1. custom2-amino-3-phenyl-5-methylpyridine was prepared
  2. additionThe reaction mixture was poured onto ice/water
  3. customthe solid removed by filtration
  4. customthe resulting precipitate was isolated by filtration (12.8 g)
  5. temperatureThe reaction mixture was heated to 80° C.
  6. stirringwith stirring for 15 hours
  7. temperatureThe reaction was cooled
  8. filtrationthe crude product was collected by filtration
  9. additionThe resultant material was treated with 1 M aqueous hydrochloric acid (200 ml)
  10. stirringstirred for 10 minutes
  11. filtrationfiltered
  12. customto remove insoluble residues
  13. filtrationthe resultant yellow precipitate was filtered
  14. customdried

Sources & evidence

ORD record
ord-d6dd21f2aac94b0fa081a6d4f405e5bd
Source dataset
uspto-grants-2009_08
Patent number
US07572791B2

Reaction notes

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