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Sodium Carbonate → HCID 57643118, compound

HRID 2112930
Notes
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Reaction equation

HRID 2112930 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:17]([O-:20])([O-])=O.[Na+].[Na+].CO[C:25]1[CH:26]=[N:27][CH:28]=[C:29](B(O)O)[CH:30]=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:26]=[N:27][C:28]([O:20][CH3:17])=[CH:29][CH:30]=3)[CH:7]=[CH:6][N:5]2[N:8]=1)=[O:13])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27630875-Methoxypyridine-3-boronic AcidHCID 57643071N-(7-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)-N′-ethylurea

Product 1

HCID 57643118HCID 57643118, compound

Reagents, catalysts & solvents 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 312751,4-DioxaneSolvent

Procedure

Compound 4, prepared as in Example 1, (120 mg, 0.42 mmol) was dissolved in dioxane (5 mL), to which was added Na2CO3 (0.50 mL of a 2 M aqueous solution) and 3-methoxy-5-pyridineboronic acid (107 mg, 0.70 mmol). Pd(dppf)Cl2 (38 mg) was added last, and the mixture heated under nitrogen at reflux for 15 h. The reaction solvent was removed and the residue filtered through a plug of silica gel (gradient 2-5% MeOH/CH2Cl2 as eluant) to give a solid which was triturated with Et2O. 1-Ethyl-3-[7-(6-methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-urea was isolated mp. 230-233° C. Anal. calcd for C15H16N6O2: C, 57.7; H, 5.2; N, 26.9. Found: C, 57.6; H, 5.2; N, 26.4.

Workup

  1. temperaturethe mixture heated under nitrogen
  2. temperatureat reflux for 15 h
  3. customThe reaction solvent was removed
  4. filtrationthe residue filtered through a plug of silica gel (gradient 2-5% MeOH/CH2Cl2 as eluant)
  5. customto give a solid which
  6. customwas triturated with Et2O

Sources & evidence

ORD record
ord-1c30c76f0615471381f6c06382bdeb0b
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07524860B2

Reaction notes

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