Dimethylformamide → HCID 57707780, compound

HRID 216894Notes

Reaction equation

HRID 216894 reaction equation
Br[CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:20]([F:23])([F:22])[F:21])[N:4]=1.I([O-])(=O)(=O)=[O:25].[Na+].CN(C=O)C>CCOC(C)=O>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[C:3]([CH:2]=[O:25])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:20]([F:23])([F:22])[F:21])[CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 23667635Sodium periodateHCID 57707841HCID 57707841, compound

Product 1

HCID 57707780HCID 57707780, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(bromomethyl)-3-(2-chlorophenyl)-5-(trifluoromethyl)quinoxaline (0.5137 g, 1.279 mmol) and sodium metaperiodate (0.1416 mL, 2.558 mmol) in DMF (8.527 mL, 1.279 mmol) was heated at 150° C. with stirring. After 3 h, the mixture was cooled to room temperature, diluted with EtOAc (100 mL), washed with brine (50 mL×2), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on a 80 g of Redi-Sep™ column using 0 to 10% gradient of EtOAc in hexane over 10 min, then 10% isocratic of EtOAc for 20 min, then 10 to 40% gradient of EtOAc in hexane over 20 min, then 40% isocratic of EtOAc for 5 min as eluent to give 3-(2-chlorophenyl)-5-(trifluoromethyl)quinoxaline-2-carbaldehyde as a yellow syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 10.15 (1H, s), 8.66 (1H, dd, J=8.6, 1.2 Hz), 8.52 (1H, d, J=7.0 Hz), 8.18 (1H, t, J=8.0 Hz), 7.53-7.67 (4H, m); LC-MS (ESI) m/z 337.0 [M+H]+.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. washwashed with brine (50 mL×2)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography on a 80 g of Redi-Sep™ column
  7. customover 10 min
  8. wait10% isocratic of EtOAc for 20 min
  9. wait10 to 40% gradient of EtOAc in hexane over 20 min

Sources & evidence

ORD record
ord-39ea129e7b3a4e08b307c0d66072682d
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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