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puried using ash chromatography to generate 4 as white
crystals. Then, 4 (1.0 eqv.), 4,4,40,40,5,5,50,50-octamethyl-2,20-
bi(1,3,2-dioxaborolane) (1.5 eqv.) and KOAc (4 eqv.) were added
to THF. The reaction was violently degassed with argon.
Pd2(dba)3 and P(Cy)3 were added and the reaction was heated to
reux for 12 hours under positive argon pressure. The reaction
was ltered through Celite® and the solvent was evaporated.
The reaction was dissolved in EtOAc and washed 3ꢄ with water.
The organic layer was collected, dried with MgSO4, and adsor-
bed onto silica. The reaction was puried with ash chroma-
tography using a hexanes/EtOAc gradient to isolate 4 (70%, 2
Example spectra for 5–37 series: 36
1H NMR (400 MHz, Chloroform-d) d 9.33 (s, 1H), 9.10 (s, 1H),
8.69 (s, 1H), 8.28 (s, 1H), 7.94–7.87 (m, 2H), 7.64 (t, J ¼ 2.0 Hz,
1H), 7.38–7.30 (m, 2H), 7.14–7.06 (m, 2H), 6.95 (dd, J ¼ 7.7, 2.0
Hz, 1H), 5.94 (s, 1H), 1.32 (s, 9H). 13C NMR (101 MHz, Chloro-
form-d) d 181.37, 163.97, 159.11, 158.35, 153.56, 148.55, 139.30,
134.73, 133.06, 129.80, 128.86, 116.53, 115.95, 113.01, 111.99,
110.83, 107.56, 91.85, 32.88, 28.54. ESIMS m/z [M + H]+ 448.
1
steps). H NMR (400 MHz, Chloroform-d) d 7.73 (d, J ¼ 8.5 Hz,
Acknowledgements
2H), 7.36 (d, J ¼ 8.4 Hz, 2H), 6.54 (s, 1H), 1.52 (s, 9H), 1.33
This work was supported by a training grant from The National
Institutes of Health (T32 GM008804), University of Arizona
startup funding, and The Caldwell Health Sciences Research
Fellowship.
(s, 12H).
Synthesis of tert-butyl (4-(6-chloropyrazin-2-yl)phenyl)-
carbamate (4a)
2,6-Dichloropyrazine (1.5 eqv.) was added to a vial containing
4 : 1 DMF–water, 4a (1.0 eqv.), and Na2CO3 (4 eqv.). The reaction
was degassed with argon for 10 minutes. Pd2(dꢀba)3 and P(Cy)3
were added and the reaction was heated to 85 C for 12 hours
under positive argon pressure. The reaction was ltered
through Celite®, diluted with EtOAc, and washed with water (50
mL, 5ꢄ). The reaction was puried with ash chromatography
Notes and references
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1H NMR (400 MHz, Chloroform-d) d 9.41 (s, 1H), 9.05 (s, 1H), 8.76
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˜
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