Iodine → HCID 59193018, compound

Participants

Reaction Steps

Polymer supported Triphenylphosphine (640 mg, 1.58 mmol) was dissolved in 25 mL of DCM followed by addition of I2 (401 mg, 1.58 mmol) and TEA (0.59 mL, 4.24 mmol) at 0° C. N′-((2R,3S)-3-(tert-butyldimethylsilyloxy)-2-(3-chloro-4-cyano-2-methylphenylamino)butanoyl)-1H-indole-5-carbohydrazide (450 mg, 1.06 mmol) in 20 mL DCM was added to the pre-cooled solution mixture of PPh3/I2/TEA system and stirred. The reaction mixture was allowed to warm to room temperature and stirred for additional 10 minutes. The reaction was quenched with 20 mL saturated sodium thiosulfate and the biphasic mixture was separated. The aqueous layer was extracted with EtOAc (3×60 mL) and the combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The resulting crude oil was purified by flash chromatography [EtOAc-hexanes (1:1) as eluent] to provide the title compound (0.403 g, 72%). 1H NMR (500 MHz, Acetone d6, δ in ppm): 10.71 (br s, 1 H), 8.25 (br s, 1H), 7.78 (d, J=9 Hz, 1 H), 7.61 (d, J=9 Hz, 1 H), 7.49-7.47 (m, 1 H), 6.86 (d, J=9 Hz, 1 H), 6.64-6.62 (m, 1H) 5.55 (d, J=9 Hz, 1 H), 5.23 (d, 9 Hz, 1 H), 4.76-4.74 (m, 1 H), 2.44 (s, 3H), 1.48 (d, J=6 Hz, 3 H), 0.87 (s, 9 H), 0.12 (s, 3 H), −0.15 (s, 3 H).

Provenance & Evidence