Fluoride Ion → HCID 22091442, compound

Participants

Reaction Steps

A solution of 390 mg (0.56 mmol) of N-({3-[(2,5-dimethoxyphenyl) (1,1,2,2-tetramethyl-1-silapropoxy)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl) (2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide in 12 mL THF is treated with 0.70 mL (0.7 mmol) 1M tetabutylammonium fluoride in THF. The mixture is stirred at room temperature for 1 hr, diluted with 15 mL sat. NaHCO3 and extracted with 3×15 mL ether. The combined organics are washed with 25 mL water and 25 mL brine. The resulting organic layer is dried over anhydrous MgSO4 and the solvent removed in vacuo to give the crude material. A small sample of the residue is prep-plate chromatographed (9% MeOH/CH2Cl2/0.5% NH4OH) to afford N-({3-[(2,5-dimethoxyphenyl)hydroxymethyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide. Mass Spec m/z (M++1) 584.

Provenance & Evidence