Hydrochloric Acid → HCID 90204264, compound

Participants

Reaction Conditions

Reaction Steps

Aqueous phosphate buffer (6.7 mL, pH=6.7) and 2,2,6,6-tetramethylpiperidine 1-oxyl (17 mg, 81 μmol) were added to a solution of (5-bromo-4-(cyclopropylmethoxy)pyridin-2-yl)methanol (300 mg, 1.16 mmol) in acetonitrile (6 mL). The mixture was warmed to 35° C. Water (4.6 mL) and a solution of sodium hypochlorite (17 mg, 14 μL, 23 μmol) in water (2.3 mL) were added within 2 h. After 20 h the mixture was cooled to ambient temperature, water (40 mL) and 2N aqueous NaOH solution (8 mL) were added. The mixture was poured onto an ice cold aqueous Na2SO3 solution (1.6 g Na2SO3 in 30 mL of water), acidified with 2N aqueous HCl solution and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with brine, dried over Na2SO4 and filtered. The filtrate was evaporated to dryness under reduced pressure to give the title compound (86 mg, 27%) as off-white solid which was used in the next step without further purification; MS (ESI, m/z): 271.9 (MH−).

Provenance & Evidence