. Author manuscript; available in PMC: 2016 Dec 1.

Published in final edited form as: Bioorg Med Chem Lett. 2015 Oct 23;25(23):5532–5535. doi: 10.1016/j.bmcl.2015.10.059

Table 1.

Effect of temperature and other parameters on directed ortho metalation of compound 5.

Trial	Scale (mmol)	TMEDA (mmol)	n– BuLi (mmol)	CuBr·DMS (mmol)	Prenyl bromide (mmol)	Solvent [conc.]	T	6 : 7	% Yield
1	6.51	14.01	14.25	6.53 ^a	7.16	Et₂O [0.07 M]	−10 °C to rt	1.0 : 1.2	36
2	7.97	16.67	17.5	7.98^a	11.93	Et₂O [0.06 M]	−20 to 0 °C to rt	1.0 : 1.9	25
3	4.18	8.67	9.2	NA	6.31	Et₂O [0.06 M]	−20 to 0 °C to rt	1.0 : 4.0	10
4	4.46	NA	9.52	4.91	4.94	THF [0.13 M]	rt	2.9 : 1.0	47
5	0.92	NA	1.95	1.02	1.11	THF [0.13 M]	rt	1.1 : 1.0	25
6	1.31	NA	2.75	1.11	1.53	THF [0.13M]	0 °C	1.0 : 1.0	39
7	4.53	NA	9.52	4.98	4.94	THF [0.13 M]	0 °C	1.8 : 1.0	51

In these experiments, copper iodide was used.