Ammonia → 3-Bromo-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid amide

Participants

Reaction Conditions

Reaction Steps

In a steel bomb, a saturated solution of ammonia in methanol was prepared by passing gaseous ammonia through methanol (250 mL) then 3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid methyl ester (14.0 g, 38.3 mol) was added. The vessel was sealed, then the reaction mixture was heated at 140° C. (15 bar) for 18 h. After this time, the reaction vessel was allowed to cool to ambient temperature then the reaction mixture was transferred to a round-bottomed flask and the solvent was removed in vacuo to afford a solid residue. The resultant solid residue was collected by filtration, washed with methanol (50 mL) and then dried to yield the desired product as a grey solid (9.47 g, 85%). 1H NMR (DMSO-D6, 400 MHz): 11.53 (s, 1H), 9.14 (d, J=2.3 Hz, 1H), 8.96 (d, J=1.1 Hz, 1H), 8.91 (d, J=1.1 Hz, 1H), 8.71 (d, J=2.3 Hz, 1H), 8.07 (s, 1H), 7.52 (s, 1H). LCMS (Method B): RT=2.49 min, M+H+=291/293.

Provenance & Evidence