Trimethylsilyldiazomethane → 2,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acid

HRID 335820Notes

Reaction equation

HRID 335820 reaction equation
[F:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([F:15])[N:3]=1.[CH3:16][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO>[F:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([Si:11]([CH3:13])([CH3:12])[CH3:14])=[C:4]([F:15])[N:3]=1.[F:1][C:2]1[N:3]=[C:4]([F:15])[C:5]([Si:11]([CH3:12])([CH3:14])[CH3:13])=[CH:6][C:7]=1[C:8]([O:10][CH3:16])=[O:9]

Participants

6

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 583348432,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acid

Product 2

HCID 583348432,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acidHCID 67383095HCID 67383095, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acid (1.17 g, 5.05 mmol) was dissolved in a mixture of DCM (20 mL) and MeOH (5 mL) and treated with (trimethylsilyl)diazomethane (2.0 m in diethyl ether, 5.0 mL, 10.00 mmol). [2,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acid was synthesized according to M. Schlosser and T. Rausis, Eur. J. Org. Chem., 2004, pp 1018-1024]. The derived solution was maintained at rt for 1 hour. Evaporation under reduced pressure and purification using the by silica gel chromatography (hexane to ethyl actetate gradient) gave the desired methyl 2,6-difluoro-5-(trimethylsilyl)nicotinate.

Workup

  1. customEvaporation
  2. customunder reduced pressure and purification

Sources & evidence

ORD record
ord-7892277ff2134201a35cd912c7b7d6e0
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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