Trimethylsilyldiazomethane → Methyl 4-iodo-2-methoxynicotinate

HRID 2377765Notes

Reaction equation

HRID 2377765 reaction equation
[I:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:11][CH3:12])[N:5]=[CH:4][CH:3]=1.[CH3:13][Si](C=[N+]=[N-])(C)C>CO>[CH3:13][O:9][C:8](=[O:10])[C:7]1[C:2]([I:1])=[CH:3][CH:4]=[N:5][C:6]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 184399404-Iodo-2-methoxypyridine-3-carboxylic acid

Product 1

HCID 58819970Methyl 4-iodo-2-methoxynicotinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-iodo-2-methoxy-nicotinic acid (1.7 g, 6.1 mmol) in 50 mL of methanol (50 ml) was added trimethylsilyldiazomethane (15 mL of a 2M solution in hexanes, 30 mmol). The mixture was stirred at ambient temperature overnight, then concentrated. The crude product was purified by flash column chromatography on silica (eluent: hexanes-ethyl acetate-triethylamine 100-10-1, then 70-30-1). 1.685 g colorless solid were isolated (94%). 1H NMR (500 MHz, acetone-d6) δ 7.93 (d, J=5.4 Hz, 1H), 7.50 (d, J=5.4 Hz, 1H), 3.92 (s, 3H), 3.90 (s, 3H);

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by flash column chromatography on silica (eluent

Sources & evidence

ORD record
ord-774e456bc3df47838bb03582a877f321
Source dataset
uspto-grants-2008_12
Patent number
US07470696B2

Reaction notes

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