(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-(4',5'-dimethyl-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 77% yield from (S)-(4,5-dimethyl-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 8.03 (d, J=11.5 Hz, 2H), 7.92-7.87 (m, 1H), 7.58-7.52 (m, 1H), 7.43 (s, 1H), 7.32 (s, 1H), 7.22 (s, 1H), 6.81 (s, 1H), 6.11-5.99 (m, 2H), 5.82-5.68 (m, 1H), 5.48-5.38 (m, 1H), 5.10-4.94 (m, 3H), 4.27-4.19 (m, 1H), 4.07-3.92 (m, J=5.0 Hz, 3H), 3.87-3.76 (m, 1H), 3.69 (s, 3H), 3.06-2.97 (m, 1H), 2.79-2.68 (m, 1H), 2.47 (s, 3H), 2.42-2.34 (m, 1H), 2.30 (s, 3H), 2.26 (s, 3H), 2.25-2.18 (m, 1H), 2.02-1.95 (m, 2H), 1.86-1.75 (m, 2H), 1.29 (s, 3H), 1.27 (s, 9H), 1.16 (d, J=6.3 Hz, 3H); LCMS (ESI, M+1): 694.35.

Provenance & Evidence