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ETHYL 4-CHLOROTHIENO[2,3-B]PYRIDINE-5-CARBOXYLATE synthesis

3synthesis methods
55503-31-6 Synthesis
4-HYDROXYTHIENO[2,3-B]PYRIDINE-5-CARBOXYLIC ACID ETHYL ESTER

55503-31-6
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Yield:59713-58-5 99%

Reaction Conditions:

with trichlorophosphate in 1,4-dioxane at 105; for 2 h;Inert atmosphere;

Steps:

4 Step 4 - Ethyl 4-chlorothieno[2,3-b]pyridine-5-carboxylate

To a mixture of ethyl 4-hydroxythieno[2,3-b]pyridine-5-carboxylate (2.60 g, 11.6 mmol) in dioxane (20 mL) was added POCl3(10.7 g, 69.8 mmol). The reaction mixture was stirred at 105 °C for 2 hour. On completion, the residue was purified by column chromatography to give the title compound (2.80 g, 99% yield) as brown.1H NMR (400 MHz, DMSO-d6) δ 8.91 (s, 1H), 8.13 (d, J = 6.0 Hz, 1H), 7.59 (d, J = 6.0 Hz, 1H), 4.43 - 4.32 (m, 2H), 1.35 (t, J = 7.2 Hz, 3H), LC-MS (ESI+) m/z 242.0 (M+H)+

References:

WO2022/147465,2022,A1 Location in patent:Paragraph 00797; 003247; 003254; 003255