Sodium Carbonate → HCID 69331987, compound

HRID 915080Notes

Reaction equation

HRID 915080 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Cl[C:8]1[N:13]=[C:12]([N:14]=CN(C)C)[C:11]([C:19]#[N:20])=[N:10][C:9]=1[C:21]1[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH:28]([CH3:30])[CH3:29])[N:22]=1.[Br:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O>O.O1CCOCC1.C(Cl)(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:14][C:12]1[C:11]([C:19]#[N:20])=[N:10][C:9]([C:21]2[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH:28]([CH3:29])[CH3:30])[N:22]=2)=[C:8]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[Br:31])[N:13]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2773294(2-Bromophenyl)boronic acidHCID 86600907HCID 86600907, compound

Product 1

HCID 69331987HCID 69331987, compoundYield 10.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
102.5 °C

Procedure

Under nitrogen atmosphere, a solution of Na2CO3 (427 mg) in water (8.8 ml) was added to a suspension of N′-[6-chloro-3-cyano-5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinyl]-N,N-dimethylimidoformamide (346 mg), (2-bromophenyl)boronic acid (503 mg) and tetrakis(triphenylphosphine)palladium (35 mg) in dioxane (22 ml) and the mixture was stirred at 100-105° C. for 4 hours. Dioxane was evaporated under reduced pressure to give a residue. The residue was dissolved in CHCl3, dried over MgSO4, concentrated under reduced pressure and purified by column chromatography on silica gel. By elution with a mixture of n-hexane and EtOAc (70:30 v/v) was obtained 3-amino-5-(2-bromophenyl)-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarbonitrile as a solid (42 mg) and by elution with a mixture of n-hexane and EtOAc (50:50 v/v) was obtained N′-[6-(2-bromophenyl)-3-cyano-5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinyl]-N,N-dimethylimidoformamide as a solid (360 mg).

Workup

  1. customDioxane was evaporated under reduced pressure
  2. customto give a residue
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography on silica gel
  6. washBy elution
  7. additionwith a mixture of n-hexane

Sources & evidence

ORD record
ord-14d6bd2b0eff4d92953878ee48f64a61
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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