Sodium Carbonate → 5-Phenylmethoxy-1-(4-pyridinylamino)-1H-indole

Participants

Reaction Conditions

Reaction Steps

To 250 ml of N-methyl-2-pyrrolidinone was added 5-(phenylmethoxy)-1H-indole-1-amine (29.7 g) and the solution was heated to 80° C. Then 4-chloropyridine hydrochloride (20.55 g) was added portionwise and the mixture was stirred for three hours, cooled, poured into water, basified with aqueous sodium carbonate and extracted with toluene. The organic/aqueous mixture was filtered to yield a solid (39 g), which was triturated with ether to yield a solid (27 g). Of this material, 3.0 g was eluted with 5% methanol/dichloromethane on a silica gel column via HPLC. The desired fractions were concentrated to yield a solid, 2.5 g, m.p. 143°-145° C.

Provenance & Evidence