5-Bromo-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine → HCID 67363366, compound

HRID 2046935Notes

Reaction equation

HRID 2046935 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

Reactant 2

HCID 584314405-Bromo-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridineHCID 59599416Methyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazol-1-yl)propanoate

Product 1

HCID 67363366HCID 67363366, compound

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).

Workup

  1. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-1be3b3c950664ee087ca6504928b75b0
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

Loading…