Selectfluor → HCID 71267869, compound

Participants

Reaction Steps

To a slurry of (2S)-ethyl 2-(tert-butoxy)-2-(2-((4-fluoro-3-methylbenzyl)carbamoyl)-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (82 mg, 0.132 mmol, 1 equiv) in acetonitrile (2.6 mL) was added Selectfluor (56 mg, 0.159 mmol, 1.2 equiv). After stirring 18 h, reaction is an orange slurry. LCMS indicated ˜50% conversion. The reaction was diluted with DCM and washed with saturated aqueous bicarbonate. The DCM layer was dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (0-10% EtOAc in hexane) to provide desired product as a yellow solid (22 mg, 26% yield). 1H NMR (500 MHz, CDCl3) δ 7.20-7.16 (m, 1H), 7.15-7.10 (m, 1H), 7.04-6.99 (m, 1H), 6.99-6.94 (m, 1H), 6.87-6.81 (m, 1H), 4.95 (s, 1H), 4.57 (d, J=5.8 Hz, 2H), 4.35 (br. s., 2H), 4.19-4.11 (m, 2H), 2.80 (s, 3H), 2.78-2.73 (m, 2H), 2.27 (s, 3H), 2.18 (br. s., 2H), 1.81 (s, 3H), 1.29 (t, J=6.9 Hz, 3H), 1.17 (s, 9H); 19F NMR (471 MHz, CDCl3) d−119.41 (s, 1F), −139.50 (s, 1F), −175.35 (s, 1F); LCMS (ESI, M+1): 639.5.

Provenance & Evidence