Sodium Iodide → 4-({[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

To 1-[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methaneamine (61 mg) were added a solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (39 mg) in 1-methyl-2-pyrrolidone (0.6 ml), triethylamine (0.056 ml), and sodium iodide (3 mg), and the mixture was stirred at 130° C. for 17 hours. After the reaction mixture was left to cool, to the reaction mixture were added N,N-dimethylformamide (0.3 ml) and water (0.1 ml), and the reaction mixture was dissolved. The reaction mixture was directly purified by preparative HPLC (101M-NH4HCO3+NH3 (pH=9.2):CH3CN=98:2 to 30:70). The active fraction was concentrated and dried to hardness to obtain 4-({[(1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (33.5 mg) as a solid.

Provenance & Evidence