4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 3-[(S)-1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5-pyridin-4-yl-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

Example 68 was synthesized according to the Suzuki coupling method described above for the synthesis of example 66, using ((S)-1-{5-Bromo-3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyrrolo[2,3-b]pyridine-1-carbonyl}-3-methyl-butyl)-carbamic acid 9H-fluoren-9-ylmethyl ester and 4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)pyridine, except that the crude product was purified by HPLC. 1H NMR (400 MHz, CD3OD): δ 8.48-8.59 (m, 3 H), 7.61 (d, J=2.0 Hz, 1H), 7.52 (dd, J=4.5, 1.5 Hz, 2H), 7.46-7.49 (m, 2 H), 7.20 (t, J=8.7 Hz, 1H), 5.34 (q, J=7.3 Hz, 1H), 1.91 (d, J=7.3 Hz, 3H). MS (ES+): m/z=386.19, 388.17 (100, 88) [MH+]. HPLC: tR=0.94 min (HPLC-ACQUITY, Purity).

Provenance & Evidence