Triphenylarsine → HCID 69524719, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloro-4-[(8-methyl-8-azabicylo[3.2.1]oct-3-yl)thio]phenyl trifluoromethanesulfonate (215 mg), lithium chloride (70 mg), triphenylarsine 32 mg) and tris(dibenzylideneacetone)-dipalladium (0) (20 mg) was stirred in N-methylpyrrolidinone (10 ml) under nitrogen for 5 minutes. To this was added 3-tributylstannylpyridine (200 mg) and the solution heated to 100° C. for 2 hours. The solution was cooled to room temperature and aqueous sodium hydroxide (10%) added to quench the reaction. The mixture was extracted three times with dichloromethane, the combined organics dried (MgSO4), filtered and evaporated to dryness. The material was purified on an SCX cartridge eluting sequentially with methanol and 2M ammonia in methanol, followed by preparative LC-MS yielding 3-{[2-chloro-4-(3-pyridinyl)phenyl]thio}-8-methyl-8-azabicylo[3.2.1]octane (54 mg)

Provenance & Evidence