(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate → (S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5'-fluoro-4'-methyl-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

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Prepared in 72% yield from (S)-(5-fluoro-4-methyl-2-(pent-4-en-2-yloxy)phenyl)boronic acid and (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate following the procedure for (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4′-fluoro-2′-((S)-pent-4-en-2-yloxy)-[1,1′-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate. 1H NMR (400 MHz, CDCl3) δ 8.02 (s, 2H), 7.96-7.92 (m, 1H), 7.56-7.51 (m, 1H), 7.48-7.41 (m, 1H), 7.32 (s, 1H), 7.14-7.09 (m, 1H), 6.81 (d, J=6.5 Hz, 1H), 6.14-5.96 (m, 2H), 5.72 (ddt, J=17.1, 10.2, 7.0 Hz, 1H), 5.43 (dd, J=17.3, 1.8 Hz, 1H), 5.12-4.95 (m, 3H), 4.22-4.10 (m, 1H), 4.07-3.94 (m, 3H), 3.82 (t, J=10.5 Hz, 1H), 3.69 (s, 3H), 3.02 (d, J=7.8 Hz, 1H), 2.73 (d, J=8.5 Hz, 1H), 2.47 (d, J=0.8 Hz, 3H), 2.40-2.33 (m, 1H), 2.31 (d, J=1.5 Hz, 3H), 2.28-2.17 (m, 1H), 1.98 (dd, J=13.9, 2.6 Hz, 2H), 1.86-1.72 (m, 2H), 1.33 (s, 3H), 1.27 (s, 9H), 1.14 (d, J=6.0 Hz, 3H); LCMS (ESI, M+1): 698.35.

Provenance & Evidence