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Grignard

[RMgX + Nitrile (Amine Pdt)]

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Examples:

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Example 1

To a solution of the SM (92 mg, 0.24 mmol) in anhydrous THF was added MeMgBr (1M in THF, 0.7 mL, 0.7 mmol) at RT. The mixture was stirred under N2 at RT for 3 h. The mixture was then added to a solution of NaBH4 (45 mg, 1.2 mmol) in MeOH (20 mL) at RT. The reaction mixture was stirred at RT for 1 h. The mixture was quenched with H2O (30 mL) and extracted with DCM (4 x 30 mL). The combined organics were washed with brine (30 mL), dried (Na2SO4), and concentrated. The residue was purified by Prep HPLC (5-95% MeOH/H2O with 0.05% NH4OH) to provide the product as a white solid. [54 mg, 56%]

[Patent Reference: WO2016011390, page 206, (20.2 MB)]

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Example 2

To a solution of the SM (180 mg, 0.49 mmol) in anhydrous toluene at RT was added EtMgBr (1M in THF, 0.6 mL, 0.6 mmol). The reaction mixture was stirred in a microwave reactor at 100 C for 20 min. After cooling to RT, the mixture was added to a solution of NaBH4 (28 mg, 0.74 mmol) in MeOH (20 mL) at 0 C. The mixture was stirred at RT for 30 min, after which time it was quenched with H2O (30 mL) and extracted with DCM (4 x 30 mL). The combined organics were washed with brine (30 mL), dried (Na2SO4), and concentrated. The resulting residue was purified by Prep HPLC (5-95% MeOH/H2O with 0.05% NH4OH) to provide the product as a yellow solid. [29 mg, 15%]

[Patent Reference: WO2016011390, page 208, (20.2 MB)]