5-Bromo-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine → HCID 67363366, compound
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([CH:11]([C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([F:20])[C:14]=3[Cl:21])[CH3:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:22][O:23][C:24](=[O:42])[C:25]([CH3:41])([N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1)[CH3:26]>>[CH3:22][O:23][C:24](=[O:42])[C:25]([N:27]1[CH:31]=[C:30]([C:2]2[CH:3]=[C:4]3[C:10]([CH:11]([C:13]4[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([F:20])[C:14]=4[Cl:21])[CH3:12])=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)[CH:29]=[N:28]1)([CH3:41])[CH3:26]Participants
3
Procedure
Prepared from 5-bromo-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]-pyridine and 2-methyl-2-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyrazol-1-yl]-propionic acid methyl ester according to the Suzuki coupling procedure described in Example 1. Purification by flash column chromatography using 0→70% EtOAc in hexanes afforded the title compound as a light yellow solid. MS (ES+): m/z 475.06/477.04 (100/68) [MH+]. HPLC: tR=2.51 min (ZQ3, polar—5 min).