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. Author manuscript; available in PMC: 2016 Apr 15.
Published in final edited form as: Bioorg Med Chem Lett. 2015 Mar 2;25(8):1761–1764. doi: 10.1016/j.bmcl.2015.02.055

Table 1.

Optimization of the stannylation on 1a.

graphic file with name nihms668669t1.jpg
entry solvent catalyst (equiv) base (equiv) yield
(%)c
1a i-PrOH Pd(PPh3)4 (0.1) DIEA (2.5) <10
2a i-PrOH PdCl2(PPh3)2 (0.1) DIEA (2.5) 0
3a i-PrOH PdCl2(PTol3)2 (0.1) DIEA (2.5) 19
4a i-PrOH Pd2(dba)3 (0.1) DIEA (2.5) 92
5b i-PrOH Pd2(dba)3 (0.025) DIEA (2.5) 97
6b toluene Pd2(dba)3 (0.025) DIEA (2.5) 37
7b THF Pd2(dba)3 (0.025) DIEA (2.5) 44
8b hexanes Pd2(dba)3 (0.025) DIEA (2.5) 14
9b MeOH Pd2(dba)3 (0.025) DIEA (2.5) 62
10b i-PrOH Pd2(dba)3 (0.025) DIEA (1.0) 94
11b i-PrOH Pd2(dba)3 (0.025) K2CO3 (2.5) 73
12b i-PrOH Pd2(dba)3 (0.025) pyridine (2.5) 0
13b i-PrOH Pd2(dba)3 (0.025) no base 68
a

2 Equiv (Bu3Sn)2.

b

1.1 Equiv (Bu3Sn)2.

c

Isolated yields.