Potassium Carbonate → HCID 118079015, compound

HRID 1485748Notes

Reaction equation

HRID 1485748 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8](C(=O)C(F)(F)F)[C@@H:7]([CH3:18])[CH2:6][N:5]2[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[F:26].C(=O)([O-])[O-].[K+].[K+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:8][C@@H:7]([CH3:18])[CH2:6][N:5]2[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])=[O:27])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 118080302HCID 118080302, compound

Product 1

HCID 118079015HCID 118079015, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude (S)-1-(6-bromo-4-(2-fluorobenzoyl)-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)-2,2,2-trifluoroethanone (0.686 g, 1.54 mmol) was dissolved in methanol (ca. 5-10 mL) and 10% aqueous potassium carbonate solution (23 mL, 1.7 mmol) was added. After 10 min, the reaction mixture was concentrated under reduced pressure in order to remove the methanol. The residue was then partitioned between ethyl acetate and water (ca. 5-8 mL). The organic layer was separated and washed with 5% aqueous sodium chloride solution (8 mL) and then concentrated under reduced pressure. The crude product was dissolved in toluene and concentrated. The residue was purified by column chromatography on silica gel (eluting with 4:1 hexanes-ethyl acetate followed by 2:1 hexanes-ethyl acetate) to afford (S)-(7-bromo-3-methyl-3,4-dihydroquinoxaline-1(2H)-yl)(2-fluorophenyl)methanone (0.415 g, 77%). MS (ESI, pos. ion) m/z 349, 351 [M+1].

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure in order
  2. customto remove the methanol
  3. customThe residue was then partitioned between ethyl acetate and water (ca. 5-8 mL)
  4. customThe organic layer was separated
  5. washwashed with 5% aqueous sodium chloride solution (8 mL)
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe crude product was dissolved in toluene
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (eluting with 4:1 hexanes-ethyl acetate followed by 2:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-e65812f191e04032b1a10e9138ddb9ed
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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