Trimethylsilyldiazomethane → HCID 67299913, compound

HRID 467620Notes

Reaction equation

HRID 467620 reaction equation
[Br:1][C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][C:5]([CH2:8][O:9][CH3:10])=[CH:6][CH:7]=1.[CH3:14][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[CH3:14][O:12][C:11]([C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[C:5]([CH2:8][O:9][CH3:10])[N:4]=1)=[O:13]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 67300137HCID 67300137, compound

Product 1

HCID 67299913HCID 67299913, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 3-bromo-6-methoxymethyl-pyridine-2-carboxylic acid (200 mg, 0.81 mmol) in benzene (4 ml) and MeOH (1 ml) was slowly added trimethylsilyl-diazomethane (0.41 ml, 0.81 mmol) at ambient temperature, and the reaction mixture was stirred for 2 hours. The solvents were removed and the residue was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried, filtered, and evaporated. The crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 158 mg (75%) of the title compound as light yellow oil.

Workup

  1. customat ambient temperature
  2. customThe solvents were removed
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0711189254eb4e9dbc2fafdc8f62a92c
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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