Triphenylphosphine → HCID 86714622, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-3,6-difluoro-4-(1H-pyrazol-5-yl)benzonitrile (0.835 mmol, 0.2 g) was dissolved in THF under nitrogen atmosphere. (S)-tert-butyl (1-hydroxypropan-2-yl)carbamate (0.835 mmol, 0.146 g) and triphenylphosphine (1.252 mmol, 0.328 g) were dissolved in THF and added to the previous mixture. The resulting mixture was cooled to 0° C. Di-tert-butyl azodicarboxylate (1.252 mmol, 0.288 g) was added in small portions and stirred under cold conditions for 10 min. The flask was warmed to RT and stirred overnight. The solvent was evaporated. The residue was dissolved in ethanol and 10% HCl(g)/EtOH solution (15 ml) was slowly added. The resulting mixture was stirred overnight. The mixture was diluted with water and extracted twice with DCM. The combined organics were washed with water. The aqueous phases were combined and the pH was adjusted to 12 with 2 M NaOH. The aqueous phase was extracted three times with DCM. The combined organics were dried, filtered and evaporated. 0.167 g of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): δ 1.17 (d, 3H), 1.31 (bs, 2H), 3.53 (bs, 1H), 3.88-4.04 (m, 1H), 4.09-4.26 (m, 1H), 6.82 (dd, 1H), 7.55 (d, 1H), 7.88 (dd, 1H).

Provenance & Evidence