Table 1.

Optimization studies for the S_NAr reaction utilizing sultam 4.

Entry	Amine	Equiv	Base	Conc. (M)	Time (min)	Temp (°C)	Yielda (%)
1	(R)-3-pyrrolidinol	1.3	Cs2CO3	0.1	30	150	NA
2	(R)-3-pyrrolidinol	4.4	—	0.1	20	150	94
3	(S)-2-pyrrolidine methanol	4.4	—	0.1	30	150	29
4	(S)-2-methoxymethyl pyrrolidine	4.3	—	0.1	50	180	NA
5	(S)-3-dimethylamino pyrrolidine	5.0	—	0.1	50	180	88
6	(R)-2-methylpyrrolidine	5.0	—	0.1	30	150	42
7	(R)-2-methylpyrrolidine	5.0	—	0.1	40	180	62b
8	(R)-2-methylpyrrolidine	5.0	—	0.1	50	180	70
9	(R)-2-methylpyrrolidine	5.0	—	0.1	60	180	35
10	(R)-2-methylpyrrolidine	5.0	—	0.5	50	180	95b
11	(R)-2-methylpyrrolidine	5.0	—	1.0	50	180	83b

^aYields are reported after flash column chromatography on silica gel. ^bCrude yield as judged by ¹H NMR.