Table 3.

Four step syntheses of compounds 28a–i – 31a–i.^a,^b

Comp		Step a		Step b		Step c		Step d
28–31	R	Time (h)	% Yield	Time (min)	% Yield	Time (h)	% Yield	Time (h)	% Yield
(min)
a	Me	26	91	15	99c	96	77	7	64e
b	Pr	5	98d	15	99c	72	51	5	75
c	n-hexyl	14	97	15	77	72	39d	12	62
d	Bn	6	98d	15	75d	64	63d	5.5	84d
e	(CH2)2Ph	10	88d	15	73	60	49	4.5	64d
f	allyl	10	87	15	58	66	54	5	55
g	3-(OPh)Bn	24	50	15	70	70	59	7	60
h	4-(CF3)Bn	22	98	15	62	96	56	7	81
i	4-(OCF3)Bn	22	86	15	72d	96	53d	19	70
Average		15	88	15	70f	77	56	8	68
Range		5–26	50–98	15	58–77f	60–96	39–77	4.5–19	55–84

^aReagents and conditions: (a) NaH, RX (alkyl halide), DMF, 0 °C–rt. (b) TFA, CH₂Cl₂, rt; then aq. NaHCO₃. (c) 2-bromopyridine, Pd₂(dba)₃, (±) BINAP, NaO^tBu, toluene, 70 °C. (d) TFA, Et₃SiH, CH₂Cl₂, rt; then aq. NaHCO₃.

^bYields are based on isolated, purified, and characterized material unless otherwise stated and optimal reaction time listed if reactions were replicated.

^cCrude yield.

^dAverage of two yields.

^eAverage of three yields.

^fCalculated for purified products only.