Hexane → Methyl 3-fluoropyridine-2-carboxylate

HRID 230775

Reaction equation

HRID 230775 reaction equation
[CH3:1]CCCCC.C[Si](C=[N+]=[N-])(C)C.[F:14][C:15]1[C:16]([C:21]([OH:23])=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1>C(O)C.CN(C=O)C>[F:14][C:15]1[C:16]([C:21]([O:23][CH3:1])=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 27627863-Fluoropyridine-2-carboxylic acid

Product 1

HCID 26746991Methyl 3-fluoropyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

A hexane solution (3 mL) of 2 M trimethylsilyldiazomethane was added to a benzene/methanol mixed solvent (1/1, 12 mL) of 3-fluoropyridine-2-carboxylic acid (250 mg), and stirred at room temperature for 30 minutes. The solvent was evaporated off under reduced pressure from the reaction solution, and the resulting residue was purified through silica gel column chromatography (chloroform/methanol=40/1) to obtain the entitled compound (238 mg).

Workup

  1. customThe solvent was evaporated off under reduced pressure from the reaction solution
  2. customthe resulting residue was purified through silica gel column chromatography (chloroform/methanol=40/1)

Sources & evidence

ORD record
ord-897de591f8e845dead7024a6fcef2167
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Linked notes

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