Dichloromethane → HCID 68225764, compound

HRID 2036634Notes

Reaction equation

HRID 2036634 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[N:6][CH:7]=1.[F:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18](I)=[C:19]([C@@H:21]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:22])[N:20]=2)[CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>O1CCOCC1.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18]([C:4]3[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[C:19]([C@@H:21]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:22])[N:20]=2)[CH:17]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 86658169HCID 86658169, compound

Product 1

HCID 68225764HCID 68225764, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-fluoropyridin-3-ylboronic acid (0.096 g, 0.68 mmol), (S)-benzyl 1-(6-fluoro-3-iodoimidazo[1,2-a]pyridin-2-yl)ethylcarbamate (0.200 g, 0.455 mmol), sodium carbonate (0.145 g, 1.366 mmol), and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride, 1:1 complex with DCM (0.019 g, 0.023 mmol) in dioxane (2.53 mL) and water (0.50 mL) was stirred at 110° C. under microwave irradiation for 2 h. Purification by MPLC (eluted with a gradient of 10-60% EtOAc in hexanes) afforded crude (S)-benzyl 1-(6-fluoro-3-(5-fluoropyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)ethylcarbamate as an off-white foam. LC-MS (ESI) m/z 409.1 [M+H]

Workup

  1. customPurification by MPLC (
  2. washeluted with a gradient of 10-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-814db9cc44b941f2920819a471871357
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

Loading…