Water → HCID 23510483, compound

HRID 1883183Notes

Reaction equation

HRID 1883183 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[C:5](I)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.O.[CH3:14][N:15](C=O)C>[C-]#N.[C-]#N.[Zn+2].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>[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[C:5]([C:14]#[N:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 23510395HCID 23510395, compound

Product 1

HCID 23510483HCID 23510483, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

A suspension of 2-methyl-8-iodoquinoxaline (730 mg), Zn(CN)2 (423 mg) and Pd(PPh3)4 (313 mg) in DMF (5 mL) was stirred at 60° C. for 5 hours. The reaction solution was cooled, and thereto was added water (10 mL), and the mixture was extracted twice with a mixture of toluene and ethyl acetate (1:1) (50 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1→4/1) to give 2-methyl-8-cyano-quinoxaline (422 mg, 93%) as red brown solid.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionthe mixture was extracted twice with a mixture of toluene and ethyl acetate (1:1) (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1→4/1)

Sources & evidence

ORD record
ord-f8e90f7a888e4c5c8cfa026605a13bb7
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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