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

HRID 1097802Notes

Reaction equation

HRID 1097802 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 rotary 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 rotary evaporator

Sources & evidence

ORD record
ord-2fc2c378559a4bfb97438b22852e7c9d
Source dataset
uspto-grants-2012_03
Patent number
US08143243B2

Reaction notes

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