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INTERMEDIATE 23 Methyl 4-(3-iodo- lH-pyrazol- 1 -yl)picolinate To 3-iodo-lH-pyrazole (625 mg, 3.22 mmol) in DMSO (15 mL) at 0 C,was added sodium hydride (60% in mineral oil, 155 mg, 3.87 mmol). The reaction was stirred for 30 min before methyl 4-fluoropicolinate (500 mg, 3.22 mmol) was added and the reaction was stirred at 90 C for 4.5 h. The reaction mixture was quenched by the addition of water and the mixture was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 0-100%) EtOAc in hexanes) to afford methyl 4-(3-iodo-lH-pyrazol-l-yl)picolinate, as a colorless solid. LCMS calc. = 329.97; found = 329.88 (M+H)+.
With methanol; sodium tetrahydroborate at 0 - 20℃; for 4h;
199.1 Step-1 : Synthesis of (4-fluoropyridin-2-yl)methanol
To a solution of methyl 4-fluoropyridine-2-carboxylate (500 mg, 3.22 mmol) in MeOH (15 mL) was added NaBHi (245 mg, 6.44 mmol) in portions at 0 °C and stirred at room temperature for 4 h. The reaction mixture was then quenched by the addition of water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to afford the title compound (420 mg, 84%) as a yellow solid.
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