Methanol → 4-(4-bromo-1-methyl-1H-pyrazol-3-yl)pyridine

HRID 1726394Notes

Reaction equation

HRID 1726394 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[N:3]1.[Br:13]Br.CO>C(Cl)(Cl)Cl.C(OCC)(=O)C>[Br:13][C:5]1[C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[N:3][N:2]([CH3:1])[CH:6]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 24408BromineHCID 200610284-(1-methyl-1H-pyrazol-3-yl)pyridine

Product 1

HCID 689237284-(4-bromo-1-methyl-1H-pyrazol-3-yl)pyridine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(1-methyl-1H-pyrazol-3-yl)pyridine 2.98 g; Example 3, Step 2) in 50 mL chloroform cooled in ice, was added dropwise, a solution of 1.15 mL bromine in 30 mL chloroform. About 15 mL methanol was added to help dissolution of the yellow precipitate that formed. After 4 hours, the reaction mixture was quenched with saturated aqueous sodium bicarbonate and diluted with dichloromethane. The dichloromethane layer was washed with saturated aqueous sodium bicarbonate, brine, dried over magnesium sulfate, filtered, and evaporated to yield the crude product as a yellow semisolid. The crude material was slurried in ethyl acetate and filtered through celite. The filtrate was evaporated to yield 4.18 g product as a yellow solid. 1H NMR (CDCl3) was consistent with the desired structure. LC/MS showed one peak with a M+1 molecular ion of m/z 240.5 by positive ESI.

Workup

  1. additionwas added dropwise
  2. dissolutiondissolution of the yellow precipitate
  3. customthat formed
  4. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  5. additiondiluted with dichloromethane
  6. washThe dichloromethane layer was washed with saturated aqueous sodium bicarbonate, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto yield the crude product as a yellow semisolid
  11. filtrationfiltered through celite
  12. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-7b2d5e9fdf12489b94ddce0ab15cf090
Source dataset
uspto-grants-2009_02
Patent number
US07491829B2

Reaction notes

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