Nitrogen → {1-[2-(1-Hydroxy-ethyl)-thiazol-4-ylmethyl]-1H-pyrazol-4-yl}-carbamic acid 2-chloro-benzyl ester

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Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [1-(2-formyl-thiazol-4-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester (155 mg, 0.41 mmol) in THF (4.0 mL) was treated at −78° C. with methylmagnesium bromide (0.41 mL of a 1M solution in THF, 0.41 mmol). The reaction mixture was stirred at −78° C. for 4.5 h then poured in sat. aq. NH4Cl (25 mL) and extracted with EA (2×25 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (90:10 CH2Cl2-MeOH) gave the title compound as a yellow oil. TLC: rf (90:10 CH2Cl2-MeOH)=0.28. LC-MS-conditions 02: tR=0.88 min; [M+H]+=393.11.

Provenance & Evidence