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To a solution of methyl 6-hydroxypyridine-2-carboxylate (300 mg, 1.96 mmol, 1.00 equiv) in DMF (1 mL) and DME (3 mL) was added of sodium hydride (90 mg, 2.25 mmol, 1.15 equiv, 60%) at 0 C followed by LiBr (339 mg, 3.90 mmol, 1.99 equiv) after a few minutes. The mixture was stirred for 15 min at room temperature then 2-(bromomethyl)-l,4-dichlorobenzene (900 mg, 3.75 mmol, 1.91 equiv) was added. The resulting solution was stirred overnight at 65 C then quenched by the addition of 2 mL of H20. The resulting solution was extracted with ethyl acetate (2x10 mL) the organic layers combined and concentrated under reduced pressure. The resulting residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 :2) to furnish 80 mg (13%) of the product 63b as a light yellow solid and 150 mg (25%) of the product 63c as a light yellow solid.
methyl 6-(2-((tert-butyldimethylsilyl)oxy)ethoxy)picolinate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
47.6%
In N,N-dimethyl-formamide; at 80℃;
[0332j Methyl 6-(2-((tert-butyldimethylsilyl)oxy)ethoxy)picolinate, Example 3.32. To a solution of methyl 6-oxo-1,6-dihydropyndine-2-carboxylate (3.31,1.0 g, 6.53 mmol) in DMF (16.33 mL) was added tert-butyl(2-iodoethoxy)dimethylsilane (2.80 g, 9.80 mmol, Sigma Aldrich). The resulting mixture was stirred at 80 °C and monitored by LCMS. Upon completion, 100 mL of saturated aqueous ammonium chloride solution was added, and the resulting mixture was extracted with EtOAc (4 x 100 mL). The combined extracts were washed with water (x 2) and brine (x 2), dried (Na2SO4) and concentrated in vacuo. The residue was purified by CombiFlash on a 120 g silica gel column using 0-80percent EtOAc gradient in heptanes as the eluent to give Example 3.32 (969 mg, 47.6percent). LCMS-ESI (POS.) mlz: 312.1 (M+H).
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