Trimethylsilyldiazomethane → Methyl 5-[(tert-butoxycarbonyl)amino]-2-fluoropyridine-4-carboxylate

HRID 276852Notes

Reaction equation

HRID 276852 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]([F:18])=[N:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][Si](C=[N+]=[N-])(C)C>CO.C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([C:15]([O:17][CH3:19])=[O:16])=[CH:13][C:12]([F:18])=[N:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 106110655-((tert-Butoxycarbonyl)amino)-2-fluoroisonicotinic acid

Product 1

HCID 57376998Methyl 5-[(tert-butoxycarbonyl)amino]-2-fluoropyridine-4-carboxylateYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To 44 g of 5-tert-butoxycarbonylamino-2-fluoro-isonicotinic acid in 100 mL of methanol and 300 mL of chloroform at 0° C. was added 200 mL of 2 M (trimethylsilyl)diazomethane in hexanes. After allowing the reaction to warm to ambient temperature and stirring for 2 hours, the solvents were removed and the crude product purified by passing through a plug of silica gel with chloroform. The product was then recrystallized from hexanes to give 32.6 g (73%) of 5-tert-butoxycarbonylamino-2-fluoro-isonicotinic acid, methyl ester: melting point 104-105° C. (decomposed); mass spectrum (m/e): M+H 270.9.

Workup

  1. customthe reaction
  2. customthe solvents were removed
  3. customthe crude product purified
  4. customThe product was then recrystallized from hexanes

Sources & evidence

ORD record
ord-a5346aeff5b448d3804b1fba6080b920
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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