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5-(difluoromethoxy)-3-methylpicolinic acid synthesis

6synthesis methods

Product Name:5-(difluoromethoxy)-3-methylpicolinic acid
CAS Number:1262860-50-3
Molecular formula:C8H7F2NO3
Molecular Weight:203.1429

5-(difluoroMethoxy)-3-Methylpicolinonitrile

1262860-51-4
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5-(difluoromethoxy)-3-methylpicolinic acid

1262860-50-3
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Yield:1262860-50-3 77%

Reaction Conditions:

with water;sodium hydroxide in ethanol at 70; for 16 h;

Steps:

45.5 Step 5. Synthesis of 5-(difluoromethoxy)-3-methylpyridine-2-carboxylic acid(C38).

Aqueous sodium hydroxide solution (1 M, 124 mL, 124 mmol) was added to a solution of C37 (7.60 g, 41 .3 mmol) in ethanol (200 mL), and the reaction mixture was stirred for 16 hours at 70 °C. It was then diluted with fe/f-butyl methyl ether (200 mL) and extracted with water (2 x 100 mL). The combined aqueous layers were washed with fe/f-butyl methyl ether (100 mL), acidified to pH 2 with 1 M aqueous hydrochloric acid, and extracted with fe/f-butyl methyl ether (2 x 200 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to afford the product as a white solid. Yield: 6.6 g, 32 mmol, 77%. LCMS m/z 203.7 [M+H]⁺.¹H NMR (400 MHz, CD3OD) δ 8.32 (br d, J=2.1 Hz, 1 H), 7.58-7.62 (m, 1 H), 7.06 (t, J_HF=72.7 HZ, 1 H), 2.64 (s, 3H).

References:

WO2015/155626,2015,A1 Location in patent:Page/Page column 89; 91

228867-86-5 Synthesis