Methanol → Methyl 5-fluoropyridine-2-carboxylate

HRID 68554Notes

Reaction equation

HRID 68554 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1.[CH3:15]O>>[CH3:15][O:13][C:12]([C:9]1[CH:8]=[CH:7][C:6]([F:5])=[CH:11][N:10]=1)=[O:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27628765-fluoropyridine-2-carboxylic Acid

Product 1

HCID 23053520Methyl 5-fluoropyridine-2-carboxylate

Conditions

Temperature
65 °C

Procedure

2.7 mL Thionylchloride was dropped to 5 g 5-fluor-pyridine-2-carboxylic acid in 50 mL methanol. The reaction was stirred for 2 h at 65° C. in a sealed micro wave vial. The solvents were removed and the residue was desolved in a mixture of DCM and methanol and filtered over silica gel. The filtrate was evaporated to give 5.9 g of the desired product.

Workup

  1. customThe solvents were removed
  2. additionthe residue was desolved in a mixture of DCM and methanol
  3. filtrationfiltered over silica gel
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-5b21e1bad20e419d945354915cd47b82
Source dataset
uspto-grants-2014_09
Patent number
US08822464B2

Reaction notes

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