Table 1. Aniline Alkylation Condition Screening^a.

entry	solvent	base	temp. (°C)	1 (HPLC area % at 245 nm)b
1	EtOH	NaOH	reflux	3
2	EtOH	NaOEt	reflux	4
3	H2O	NaOH	80
4	acetonitrile	K2CO3	reflux	6
5	acetonitrile	DBU	reflux	3
6	acetone	Cs2CO3	reflux	49
7	acetone	K2CO3c	reflux	6
8	acetone	K2CO3d	reflux	46
9	THF	NaH	20	40
10	DMF	NaH	20	44
11	DMF	NaOH	80	76
12	NMP	NaOH	80	68
13	diglyme	NaOH	80	82
14	diglyme	KOH	80	85
15	DMSO	NaOH	80	94
16	DMSO	KOH	80	93
17	sulfolane	NaOH	80	90
18	sulfolane	NaOHe	80	87

^aGeneral reaction conditions: aniline (2, 100 mg, 1 equiv), BBMO (3, 1.2 equiv), and base (2.5 equiv) were added to the solvent (2 mL) in a small vial. This mixture was heated to the listed temperature with stirring for 16 h.

^bThese HPLC data are from an IPC sample taken at the end of the reaction. The percentages are not adjusted for response factors.

^cKI (0.1 equiv) was added to the reaction mixture.

^dTBAI (0.1 equiv) was added to the reaction mixture.

^eDelivered as 50 wt % NaOH (aq).