3-[1-(2,6-Dichlorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine → HCID 67364074, compound

Participants

Reaction Steps

((S)-1-{5-Bromo-3[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-pyrrolo[2,3-b]pyridine-1-carbonyl}-3-methylbutyl)carbamic acid 9H-fluoren-9-ylmethyl ester was treated with 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrazol-1-yl]piperidine hydrochloride according to typical Suzuki coupling procedure described for synthesis of 3-[1-(2,6-Dichlorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine in example 1, to give the title compound. 1H NMR (400 MHz, DMSO-d6): δ=1.70-1.80 (m, 2H), 1.83 (d, J=7.1 Hz, 3H), 1.94 (dd, J=11.6, 2.0 Hz, 2H), 2.08 (br s, 1H), 2.57 (td, J=12.3, 2.3 Hz, 2H), 3.03 (ddd, J=12.6, 2.9, 2.7 Hz, 2H), 4.17 (tt, J=11.6, 4.1 Hz, 1H), 5.16 (q, J=7.2 Hz, 1H), 7.33 (d, J=1.8 Hz, 1H), 7.36-7.44 (m, 2H), 7.48-7.65 (m, 1H), 7.56 (d, J=0.5 Hz, 1H), 8.03 (s, 1H), 8.39 (d, J=2.0 Hz, 1H), 11.51 (d, J=1.8 Hz, 1H). MS (ES+): m/z 458.07/460.05 (100/70) [MH+]. HPLC: tR=2.53 min (ZQ3, polar—5 min).

Provenance & Evidence