Sodium Carbonate → HCID 11644859, compound

HRID 2112929Notes

Reaction equation

HRID 2112929 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])[N:10]=[C:4]2[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[CH:24]=1>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:4]2[CH:3]=[C:2]([C:25]3[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=3)[CH:7]=[CH:6][N:5]2[N:8]=1)=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 57643071N-(7-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)-N′-ethylurea

Product 1

HCID 11644859HCID 11644859, compound

Reagents, catalysts & solvents 2

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

Procedure

1-(7-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-ethyl-urea (4) (80 mg, 0.28 mmol) was dissolved in dioxane (2 mL), to which was added 2 M Na2CO3 (0.30 mL) and 3-pyridinylboronic acid (38 mg, 0.31 mmol). Pd(dppf)Cl2 (13 mg) was added last, and the mixture heated under nitrogen at reflux for 1.5 h. The reaction solvent was removed under reduced pressure and the residue filtered through a plug of silica gel (5% MeOH/CH2Cl2 as eluant) to give a solid, which was triturated with Et2O. 1-Ethyl-3-(7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea was isolated mp. 230-233° C.

Workup

  1. temperaturethe mixture heated under nitrogen
  2. temperatureat reflux for 1.5 h
  3. customThe reaction solvent was removed under reduced pressure
  4. filtrationthe residue filtered through a plug of silica gel (5% MeOH/CH2Cl2 as eluant)
  5. customto give a solid, which
  6. customwas triturated with Et2O

Sources & evidence

ORD record
ord-080b38a74d1a44ae8c876db5476e87ea
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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