Iodine → HCID 89964713, compound

Participants

Reaction Steps

To a solution of magnesium turnings (0.083 mL, 5.80 mmol) and iodine (10 mg) in 2-MeTHF (6 mL) under N2 at room temperature was slowly added a solution of 2-bromonaphthalene (1.0 g, 4.83 mmol) in 2-MeTHF (4 mL). After addition, the mixture was stirred at room temperature for 18 h. The mixture was cooled to −78° C., and a solution of (S,E)-2-methyl-N-(2H-pyrano[3,2-b]pyridin-4(3H)-ylidene)propane-2-sulfinamide (0.490 g, 1.942 mmol) in 2-MeTHF (3 mL) was added dropwise. The mixture was then stirred at −78° C. for 1 h and at room temperature for 5 h. The mixture was quenched with saturated NH4Cl (1.5 mL). The mixture was then extracted with EtOAc (2×5 mL). The combined organic extracts were dried over MgSO4, concentrated, and purified by silica gel column chromatography using ISCO (30-60% EtOAc/hexanes) to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 381.0 (M+H)

Provenance & Evidence