5-Difluoromethyl-pyridine-2-carboxylic Acid Methyl Ester synthesis
- Product Name:5-Difluoromethyl-pyridine-2-carboxylic Acid Methyl Ester
- CAS Number:1346148-42-2
- Molecular formula:C8H7F2NO2
- Molecular Weight:187.14
67-56-1
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Yield:1346148-42-2 74%
Reaction Conditions:
with palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride;anhydrous potassium acetate in methanol at 90; under 2585.81 Torr; for 16 h;Inert atmosphere;
Steps:
1.ii Step ii.
In a steel reaction vessel, a solution of 2-bromo-5-(difluoromethyl)pyridine (3.0 g, 14 mmol) in MeOH (30 mL) was degassed with argon gas for 20 min then of potassium acetate (2.82 g, 28.8 mmol, 2.0 eq.) and Pd(dppf)Cl2 (527 mg, 0.72mmol, 0.05 eq.) were added and the mixture was degassed with argon gas for 5 min. The reaction mixture was stirred under CO gas (50 psi) at 90 °C for 16 h. The reaction mixture was filtered through a pad of CELITE and the filtrate was evaporated. Obtained crude material was purified by column chromatography using silica gel (100-200 mesh) and 10% EtOAc in petroleum ether as eluent to afford methyl 5-(difluoromethyl)picolinate (2.0 g, 74% yield) as a pale-yellow solid. LCMS m/z found 188.2 [M+H]+; RT = 1.15 min (Method E).
References:
WO2021/229302,2021,A1 Location in patent:Page/Page column 144; 403-404
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