Triacetoxyperiodinane → HCID 58847437, compound

Participants

Reaction Steps

To a solution of Dess-Martin reagent (48 mg, 0.114 mmol) in 1.5 mL of CH2Cl2 cooled to 0° C., was added dropwise a solution of 2-hydroxy-2-{4-[2-((R)-3-methoxy-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-phenyl}-N-methyl-acetamide (Example 77) (42 mg, 0.095 mmol) in 1.5 mL of CH2Cl2. The mixture was stirred at 0° C. to room temperature for one hour. Saturated aqueous NaHCO3 solution was added, and the mixture was extracted with CH2Cl2 and a small amount of MeOH. The combined organic phase was dried over Na2SO4, concentrated, and purified by flash column chromatography eluting with EtOAc:CH2Cl2:MeOH (1:1:0.04) to provide 30 mg white solid as the compound of Example 78. 1H NMR (300 MHz, CD3OD) δ 8.47 (d, 1H, J=5.47 Hz), 8.17 (d, 2H, J=8.66 Hz), 7.28 (d, 2H, J=8.66 Hz), 7.78–7.62 (m, 1H), 6.81 (d, 1H, J=5.47 Hz), 4.08–3.76 (m, 5H), 3.75–3.52 (m, 3H), 2.78 (s, 3H), 2.30–1.97 (m, 2H). LCMS (ESI+) [M+H]/z Calc'd 440, found 440. Anal. (C22H21N3O5S.0.4CH2Cl2) C, H, N.

Provenance & Evidence