Iodoethane → HCID 68786219, compound

Participants

Reaction Conditions

Reaction Steps

Into an 18 mL vial was added P-374 (65 mg, 0.16 mmol), THF (3 mL), and the solution was cooled to 0° C. NaH (9 mg, 0.23 mmol) was added and the suspension was stirred at room temperature for 15 minutes. EtI (25 uL, 0.31 mmol) was added and the reaction was stirred for 1 hour at room temperature. Water was added and the product was extracted with EtOAc (3×3 mL). The organics were washed with water, brine, and concentrated. To the residue was added 2 mL of 4N HCl/dioxane. After stirring to dissolve, the solution was concentrated. The resulting residue was triturated with ether, filtered, washed with ether, and dried to give P-461 (51 mg, 65%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) 8.63 (br s, 2H), 8.07 (br s, 1H), 7.60 (d, J=7.9 Hz, 1H), 7.50-7.33 (m, 4H), 7.29 (d, J=5.8 Hz, 1H), 6.97 (d, J=8.3 Hz, 1H), 4.51 (s, 2H), 4.09 (br s, 2H), 3.74 (s, 3H), 3.57 (s, 2H), 3.31 (s, 2H), 3.19-3.10 (m, 2H), 1.10-0.97 (m, 3H) ppm. LC/MS=84.2%, 454.2 (APCI+).

Provenance & Evidence