Ammonium Chloride → HCID 178431104, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 1-(trans-4-{[tert-butyl(dimethyl)silyl]-oxy}cyclohexyl)-4-iodo-1H-pyrazole (1.14 g, 2.80 mmol) in THF (30.0 mL) was cooled to 0° C. and treated with isopropylmagnesium chloride (2.0 M in THF, 2.31 mL, 4.63 mmol), added dropwise under an atmosphere of nitrogen over 5 min. The reaction mixture was stirred at 0° C. for another 1 h, then treated 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.95 mL, 5.6 mmol) and stirred at RT for another hour. The mixture was treated with saturated aqueous NH4Cl (10 mL) and extracted with EtOAc (3×20 mL). The extracts were washed with water (10 mL), brine (15 mL), and dried over Na2SO4. Solvent was removed under reduced pressure to give a residue which was purified by flash chromatography (10% EtOAc:hexane) to provide 1.10 g (96%) of the title compound. MS (ESI): 405.95 [M+H]+; HPLC tR=3.21 min.

Provenance & Evidence