Sodium Carbonate → HCID 68835864, compound

HRID 2112976Notes

Reaction equation

HRID 2112976 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])[N:10]=[C:6]2[CH:5]=[C:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:3]=1.[CH3:23][O:24][C:25]1[N:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:15]([NH:14][C:12]([NH:11][C:9]1[N:10]=[C:6]2[CH:5]=[C:4]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:3]=[C:2]([C:28]3[CH:29]=[N:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=3)[N:7]2[N:8]=1)=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 86618027HCID 86618027, compound

Product 1

HCID 68835864HCID 68835864, compound

Reagents, catalysts & solvents 2

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

Procedure

To a mixture of 1-(5-chloro-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-ethyl-urea (0.2 g, 0.63 mmol) obtained in step 1, 6-Methoxy-pyridine-3-boronic acid (0.12 g, 0.78 mmol), and sodium carbonate (0.71 mL of a 2 M aqueous solution) in dioxane (6 mL) was added the catalyst Pd(dppf)Cl2 (30 mg, 5 mol %) and the resulting mixture was heated to reflux for 36 hours. The solvent was removed under reduced pressure. Purification using silica gel chromatography (2-10% MeOH/CHCl3) gave the title compound as a solid LCMS (APC+) 390.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 36 hours
  3. customThe solvent was removed under reduced pressure
  4. customPurification

Sources & evidence

ORD record
ord-f9442e4387f44e32975383d77a5f22ea
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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