Tetrahydrofuran → HCID 58342010, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 4-[N-(2-tert-butyldimethylsilylsilanyloxyethyl)-N-methyl-4-{(E)-2-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]ethenyl}aniline (0.18 g, 0.362 mmol) in a mixture of dry THF (5 ml) and dry DMF (3 ml) at 0-5° C. was added a solution of TBAF in THF (1 M, 800 μl, 0.800 mmol). The reaction mixture was stirred at 0-5° C. for 5 min and then left to rise to room temperature and stirred for a further 50 min. A solution of saturated ammonium chloride (25 ml) was added to the reaction mixture and this was extracted with DCM/MeOH (1:1, 5×30 ml). The combined organics were washed with brine (40 ml), dried (Na2SO4) and the solvent removed under reduced pressure to give a yellow oil that slowly solidified at room temperature. The solid was purified by flash chromatography (10:1 DCM/MeOH) to give the title compound (0.136 g, 98%) as a yellow solid.

Provenance & Evidence