Methyl iodide → Methyl 2-fluoro-4-(trifluoromethyl)nicotinate

HRID 587578

Reaction equation

HRID 587578 reaction equation
[F:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:4][N:3]=1.[C:15]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[F:1][C:2]1[C:7]([C:8]([O:10][CH3:15])=[O:9])=[C:6]([C:11]([F:12])([F:13])[F:14])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 283077662-Fluoro-4-(trifluoromethyl)pyridine-3-carboxylic acid

Product 1

HCID 58577652Methyl 2-fluoro-4-(trifluoromethyl)nicotinateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-fluoro-4-(trifluoromethyl)pyridine-3-carboxylic acid (1.06 g) and K2CO3 (0.701 g) in DMF (dry) (10 mL) was added MeI (0.317 mL). The mixture was stirred at room temperature for 3 h. The mixture was directly purified by column chromatography (silica gel, EtOAc/hexane) to give the title compound (1.13 g, containing EtOAc and hexane, ca. 75% purity).

Workup

  1. customThe mixture was directly purified by column chromatography (silica gel, EtOAc/hexane)

Sources & evidence

ORD record
ord-e947ef367a9e42bd8070dcc3c22982cd
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Linked notes

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