Water → HCID 89726761, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 5-fluoro-2-nitroaniline (329 mg), 1-Boc-3-hydroxyazetidine (346 mg) and NaH (65% in oil, 62.4 mg) in DMF (6 mL). The mixture was heated at 100° C. for 7 h, cooled down, and diluted water. The solvent was coevaporated with toluene. The residue was taken up in EA/water and the org. layer was evaporated in vacuo. The residue was purified by CC (Biotage, SNAP 25 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 8 for 4CV, 8 to 66 over 10CV, 66 for 2CV) to afford 519 mg of orange foam. LC-MS (B): tR=0.88 min. 1H-NMR (CDCl3): 8.11 (d, 1H, 9.5 Hz); 6.22 (s, NH2); 6.19 (dd, 1H, 2.6 Hz and 9.5 Hz); 5.97 (d, 1H, 2.5 Hz); 4.90 (m, 1H); 4.33 (m, 2H); 4.02 (m, 2H); 1.47 (s, 9H).

Provenance & Evidence