Isopropyl isocyanate → HCID 66787495, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the hydrochloride salt of 5-bromo-3-pyridinemethanamine (CAS#135124-70-8, 176 mg, 0.65 mmol) in 1,4-dioxane (10 mL) at room temperature was added diisopropylethylamine (0.550 mL, 3.27 mmol) followed by isopropyl isocyanate (CAS#1795-48-8, 0.13 mL, 1.3 mmol). The reaction was then heated to 80° C. and stirred for 15 minutes. The reaction was then cooled to room temperature, quenched with methanol, and stirred for an additional 15 minutes. The resulting solution was then concentrated in vacuo to near dryness, and diluted with dichloromethane and brine. The layers were separated and the aqueous layer was extracted two additional times. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to furnish 1-(5-bromo-pyridin-3-ylmethyl)-3-isopropyl-urea without the need for further purification; MS: (ES+) m/z 271.9 (M+H)+.

Provenance & Evidence