Tetrahydrofuran → HCID 86648142, compound

Participants

Reaction Steps

Compound 68 (200 mg, 0.44 mmol) was treated with hydrogen in the presence of 10% Pd on carbon (20 mg). After 16 h stirring, the mixture was filtered through Celite and the solvent was evaporated off in vacuo to give the intermediate amino aniline product. This was then reacted with triphosgene (195 mg, 0.70 mmol) in the presence of triethylamine (260 uL, 0.70 mmol) in THF (15 mL). After 1 h stirring at room temperature a white precipitate was filtered off and the solvent was evaporated off in vacuo to give a crude residue of isocyanate aniline. This was used straight away in the following step. Isocyanate intermediate was dissolved in THF (10 mL). The solution was cooled to 0° C. Benzofuran-2-ylmethanol 59 (100 mg, 1.35 mmol) was added and the resulting mixture was stirred at room temperature for 16 h. The mixture was cooled on ice and TBAF (996 μL, 3.38 mmol) was added dropwise over 5 min. The resulting mixture was allowed to warm to room temperature and then stirred for 20 min. THF was evaporated off in vacuo. The intermediate was dissolved in pyridine (5 mL) and to this was added methane sulphonyl chloride (12.5 μL, 0.16 mmol). The mixture was stirred at room temperature for 1 h. Pyridine was evaporated off in vacuo and the crude product was purified by flash chromatography, eluting with hexane:EtOAc (3:1) to give 69 (5 mg, 2%) as a white solid. m/z=408.07 (M+H), 837.16 (2M+H).

Provenance & Evidence