Tetrabutylammonium Fluoride → HCID 68771290, compound

Participants

Reaction Steps

2-(tert-Butyl-dimethyl-silanyl)-4-(hydroxy-naphthalen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide (Intermediate-I1) (2.6 g, 5.4 mmol) in THF (30 mL) was treated with tetrabutylammonium fluoride (TBAF) (5.8 mL of a 1M soln) at rt for 1 h. The reaction mixture was subjected to an aqueous work-up and the product was purified by chromatography on silica gel with 66% EtOAc:hexane to give 4-(hydroxy-naphthalen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide as a white solid, 1.54 g (80%). 4-(Hydroxy-naphthalen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide (1.0 g, 3.0 mmol) was deoxygenated with TES in TFA according to the applicable procedures outlined in Method A to give 4-naphthalen-2-yl-methyl-imidazole-1-sulfonic acid dimethylamide (Intermediate-I2) as a white solid 0.55 g, (58%).

Provenance & Evidence