HCID 89422961, compound → HCID 71285061, compound

Participants

Reaction Steps

A mixture of 5-allyl-1-(2,4-dimethoxybenzyl)-6-(2-((dimethylamino)methyl)-1H-indol-5-yl)-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid (45 mg, 0.085 mmol), prepared according to the procedure described in Example 164, Steps 1-6, and Pd/C (10 mg, 10%) in EtOAc (1 mL) was stirred under H2 (1 atm) at room temperature for 2 h. The solvent was evaporated and the residue was chromatographed (0-2.5% MeOH in CH2Cl2) to give the intermediate of 1-(2,4-dimethoxybenzyl)-6-(2-((dimethylamino)methyl)-1H-indol-5-yl)-4-hydroxy-2-oxo-5-propyl-1,2-dihydropyridine-3-carboxylic acid. LC-MS 489.2 [M+H]+, RT 1.17 min. This intermediate was stirred in TFA (0.5 mL) and TIPS-H (0.5 mL) at room temperature for 15 h, and then the mixture was concentrated to dryness. The residue was dissolved in CH2Cl2 (0.5 mL), then HCl (2.0M in Et2O, 1.0 mL) was added. The precipitate was collected by filtration and washed by ether to afford the title compound as an off-white solid (15 mg, 44% over 2 steps).

Provenance & Evidence