Trimethylsilyldiazomethane → Methyl 2-chloro-5-(trifluoromethyl)nicotinate

HRID 72432

Reaction equation

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

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 2-chloro-5-(trifluoromethyl)nicotinic acid (500 mg, 2.21 mmole, available from Apollo #PC9219) in a mixture diethyl ether/methanol (5 ml)/(15 ml) was cooled to −20° C. then trimethylsilyldiazomethane (2M solution in diethyl ether) (2.15 ml, 4.43 mmol) was added dropwise. The reaction mixture was stirred at −20° C. for 1 h then allowed to warm to room temperature. After solvent evaporation, the obtained residue was loaded on SPE-Si cartridge (10 g) eluting with a mixture cyclohexane/dichloromethane from 80/20 to 60/40. Collected fractions, after solvent evaporation, afforded the title compound (D66) (300 mg)

Workup

temperatureto warm to room temperature
customAfter solvent evaporation
washeluting with a mixture cyclohexane/dichloromethane from 80/20 to 60/40
customCollected fractions, after solvent evaporation

Sources & evidence

ORD record: ord-248d742fe9914443b5a1b8677321059c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828987B2

Linked notes

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