Diazald → HCID 71112438, compound

Participants

Reaction Steps

To a solution of KOH (119 equiv) in H2O and ethanol heated to 65° C. was added N-methyl-N-nitroso-p-toluenesul-fonamide (3 equiv) in ether. The diazomethane ether solution was distillated and collected at −78° C. Then, a solution of vinyl-containing material (e.g., 8,8-dimethyl-3-(2-(pyridin-2-yl)vinyl)-8,9-dihydro-6H-pyrido[2,1-b]-quinazolin-11(7H)-one, 1 equiv) and Rh(OAc)2(0.1 equiv) in CH2Cl2 was added to the ethereal diazomethane solution and stirred overnight at room temperature. The mixture was quenched with 10% acetic acid in ethyl acetate, diluted with H2O and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography (EtOAc:n-hexane=1:3) to give the cyclopropanated product (e.g., 8,8-dimethyl-3-(2-(pyridin-2-yl)cyclopropyl)-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one).

Provenance & Evidence