Dimethylformamide → HCID 86585285, compound

Participants

Reaction Steps

Into a round bottom flask was placed methyl 3-(phenylmethoxy)indole-2-carboxylate (50 mg) along with DMF (1.0 mL), THF (1.0 mL) and 10 mg of a NaH suspension (60% in oil). To this stirred mixture was added 4-tert-butylbenzyl bromide and allowed to stir at room temperature overnight. At this time, the reaction mixture was diluted with H2O, poured into a teflon fritted cartridge and extracted with CH2Cl2. The filtrate was concentrated and then treated with THF/H2O (5.0 mL, 1:1), MeOH (2.0 mL), NaOH (1 mL of a 1N aq. solution) and allowed to stir at room temperature overnight. At this time, the reaction mixture was acidified to pH 4 with an aqueous 1N HCl solution, diluted with 2 mL H2O, extracted with CH2Cl2 through a teflon fritted cartridge as above and the filtrate was concentrated. The resulting crude carboxylic acid was taken up in THF (2.0 mL) and treated with i-Pr2NEt (0.1 mL), MsCl (10 μL) followed by 3-aminopyridine (50 mg) as described previously for the preparation of example 166. After work-up and purification by flash chromatography 10.6 mg of the title amide was isolated.

Provenance & Evidence