Sodium Carbonate → HCID 66864112, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-1-[(4-methylphenyl)sulfonyl]-1,2,5,6-tetrahydropyridine-3-carbaldehyde (1 eq) obtained in step II of example 200 in DMSO was added Na2CO3(4.0 eq) and sarcosine hydrochloride (2.0 eq) at room temp and the reaction mixture was stirred for 1.5 hr at 40° C. Reaction mass was then quenched with water and extracted with ethyl acetate. Organic layer was separated and dried over anhydrous Na2SO4, concentrated under reduced pressure to afford crude product, which, was dissolve in DMF and added to the mixture of tBuOK (1.0 eq) in DMF at 0° C. and stirred at room temperature for 2 h Reaction mass was quenched in water and extracted with ethyl acetate. Organic layer was separated dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded ethyl 1-methyl-5-[(4-methylphenyl)sulfonyl]-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate.

Provenance & Evidence