Selenium Dioxide → HCID 84819808, compound

HRID 1620401Notes

Reaction equation

HRID 1620401 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([CH3:18])[N:11]=1.[Se](=O)=[O:20]>COCCOCCOC.C(O)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([CH:18]=[O:20])[N:11]=1

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 67491765HCID 67491765, compound

Product 1

HCID 84819808HCID 84819808, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8150DiglymeSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-(2,4-difluorophenylamino)-2-methylnicotinonitrile (350 mg, 1.4 mmol) and selenium dioxide (238 mg, 2.14 mmol) in 1-methoxy-2-(2-methoxyethoxy)ethane (7.00 mL) and 0.2 mL of glacial acetic acid was heated in an oil bath at 120° C. for 10 min. The temperature of the oil bath was slowly warmed to 155° C. in 30 min and stirred at this temperature for 3 h. The reaction mixture was cooled to RT, filtered through a pad of Celite washing with EtOAc, and concentrated. The remaining brown solution was purified on an ISCO 12 g column and the product eluted with 50-80% EtOAc in hexanes to afford 6-(2,4-difluorophenylamino)-2-formylnicotinonitrile in residual amount of 1-methoxy-2-(2-methoxyethoxy)ethane. MS (ESI, pos.ion) m/z: M+1=260.0

Workup

  1. temperatureThe temperature of the oil bath was slowly warmed to 155° C. in 30 min
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through a pad of Celite
  4. washwashing with EtOAc
  5. concentrationconcentrated
  6. customThe remaining brown solution was purified on an ISCO 12 g column
  7. washthe product eluted with 50-80% EtOAc in hexanes

Sources & evidence

ORD record
ord-bd87e149c82b4fa48ce579c0023fa22f
Source dataset
uspto-grants-2014_07
Patent number
US08772481B2

Reaction notes

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