4-Fluorobenzaldehyde → HCID 57659776, compound

Participants

Reaction Conditions

Reaction Steps

To a flame-dried flask under nitrogen was added THF (3 mL) followed by isopropylmagnesium chloride (2M THF, 0.708 mL) and the mixture cooled to −10° C. n-BuLi (1.6M Hexane, 1.77 mL) was added dropwise and stirred for 30 minutes. The reaction was cooled to −78° C. and tert-butyl (3-iodo-1-(methoxymethyl)-1H-pyrazol-4-yl)methyl(4-(trifluoromethyl)phenylsulfonyl)carbamate (43) (815 mg, 1.42 mmol) in THF (3 mL) was added dropwise and stirred for 30 minutes. 4-Fluorobenzaldehyde (0.91 mL, 8.52 mmol) was added neat and stirred for 1 hr before quenching with aq. ammonium chloride (5 mL). The aqueous layer was discarded and the reaction was concentrated in vacuo. The resulting crude product was purified by column chromatography using EtOAc/hexane gradients to yield tert-butyl (3-((4-fluorophenyl)(hydroxy)methyl)-1-(methoxymethyl)-1H-pyrazol-4-yl)methyl(4-(trifluoromethyl)phenylsulfonyl)carbamate (44) (447 mg, 55%) as a clear oil.

Provenance & Evidence