To further understand how the nature of the chloroaniline and heteroaryl bromide substrates influenced the chemoand regioselectivity of both bond-forming steps, a series of test reactions were undertaken (Scheme 2). Exchanging 6bromoisoquinoline (6a) for isoquinoline (10) formed dimethoxyphenazine (11) and the tertiary aniline (12) in 35% and 25% isolated yield, respectively (Scheme 2a). No dihydrophenazine was isolated from the reaction, which suggests an in situ oxidation occurred. No reaction occurred when isoquinoline (10) was the coupling partner with 1-chloro-3-methoxybenzene (13, Scheme 2b). Only secondary aniline (15) was isolated when para-anisidine (14) was reacted with 6-bromoisoquinoline (6a, Scheme 2c). Taken collectively, these test reactions highlighted the following requirements for the preparation of the tetracyclic core: (i) the aryl bromide is essential and prevents dimerization of the chloroaniline, (ii) whilst the absence of a bromo substituent in the heteroaryl substrate results in C-H activation at the same site, there is little regiocontrol, (iii) a chloro substituent is essential for C-arylation.