Trimethylsilyldiazomethane → methyl 5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1994096Notes

Reaction equation

HRID 1994096 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12]([OH:14])=[O:13].[CH3:15][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:10])([F:11])[F:9])[C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27738065-Chloro-1-Methyl-3-(Trifluoromethyl)-1H-Pyrazole-4-Carboxylic Acid

Product 1

HCID 1473689methyl 5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (1.00 g, 4.38 mmol) in benzene (5.83 mL) and methanol (2.92 mL) at room temperature was added 2M trimethylsilyldiazomethane (8.75 mL). The resulting solution was stirred at room temperature for 3 hours. Solvent was removed at reduced pressure on a rotory evaporator to yield the title compound (1.06 g, 4.38 mmol, 100% yield) as a white solid. MS m/z 243 (MH+). 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 3.82 (s, 3H) 3.89 (s, 3H).

Workup

  1. customSolvent was removed at reduced pressure on a rotory evaporator

Sources & evidence

ORD record
ord-de7e844bf95a4e8ba72c7580ae6d3089
Source dataset
uspto-grants-2010_01
Patent number
US07652004B2

Reaction notes

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