Iodine → HCID 67111148, compound

Participants

Reaction Steps

Iodine (17.5 mg, 0.069 mmol, 1.3 equiv) was added to a stirring biphasic solution of N-(3-{3-[1-ethyl-5-(4-formylphenoxy)-1H-pyrazol-3-yl]phenyl}oxetane-3-yl)-2,2,2-trifluoroethanesulfonamide (27 mg, 0.053 mmol, 1.0 equiv) in 1 mL THF and 0.53 mL of concentrated NH4OH (28% solution). After stirring for 7 hours, aqueous Na2S2O3 was added (1 mL of a 5% solution) and the reaction mixture was extracted with diethyl ether. The organic layer was dried over magnesium sulfate. The dried solution was filtered and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (0-60% ethyl acetate:hexanes) to give N-(3-{3-[5-(4-cyanophenoxy)-1-ethyl-1H-pyrazol-3-yl]phenyl}oxetane-3-yl)-2,2,2-trifluoroethanesulfonamide (17 mg, 0.034 mmol, 65% yield). HRMS Calc'd (M+1)+507.1308. Found: 507.1305. (400 MHz, 1H, δ-CDCl3) 1.45 (3H, t, J=7.2), 3.04 (2H, q, J=8.6), 4.10 (2H, q, J=7.2), 5.04 (2H, d, J=7.1), 5.16 (2H, d, J=7.1), 5.66 (1H, br s), 6.11 (1H, s), 7.22 (2H, d, H=8.6), 7.36 (1H, d, J=7.9), 7.51 (1H, t, J=8.0), 7.70 (2H, d, J=8.6), 7.80 (2H, m).

Provenance & Evidence