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. Author manuscript; available in PMC: 2015 Jan 17.
Published in final edited form as: J Org Chem. 2013 Oct 31;79(2):473–486. doi: 10.1021/jo4020358

Table 1.

Optimization of the iridium-catalyzed borylation at C2 of 6-methoxytryptamine 26.

graphic file with name nihms-533822-t0020.jpg

Entry HBPin
equiv		 Ir catalyst
(mol%)		 bipyridyl ligand
(mol%)		 temp
(°C)		 solvent resulta
1 1 5 10 70 THF No reaction
2 2.6 3 6 80 THF 28: 93%
3 2 5 10 45 THF 27:28 = 2.2:1b, 48%
4 2 5 10 45 CH2Cl2 27: 55%
5 2.5 5 10 45 CH2Cl2 27:28 = 4.5:1b, 66%
6 2.2 10 10 23 CH2Cl2 27: 67%
a

Isolated yield.

b

Ratio of 27 to 28 was determined by 1H NMR.