Pyridine → N-3',4'-Dihydro-2'H-spiro[1,3-dioxane-2,10'-pyrimido[1,2-a]indol]-8'-ylbenzamide

Participants

Reaction Steps

To a cold solution of 3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′-pyrimido[1,2-a]indol]-8′-amine (0.290 g, 1.44 mmol) and pyridine (0.349 mL, 4.32 mmol, 3 eq) in anhyd. CH2Cl2 (14.4 mL) was added benzoyl chloride (0.200 mL, 1.73 mmol, 1.2 eq) drop-wise with cooling in an ice bath under a dry N2 atmosphere. After stirring 2 hr. at room temperature the reaction was added to water. The reaction mixture was washed with Et2O (3×), basified with 2.5N NaOH and extracted with EtOAc (4×). The combined organic extracts were concentrated. The crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3O H/NH4OH (98/1/1) to give the title compound as a yellow solid (0.079 g, 15% yield). NM (300 Mz, DMSO-d6): consistent.

Provenance & Evidence