Formic Acid → (S)-4-acetyl-3-methyl-7-(4-(methylsulfonyl)phenyl)-3,4-dihydroquinoxaline-1 (2H)-carbaldehyde

HRID 1485757Notes

Reaction equation

HRID 1485757 reaction equation
[CH:1]([O-:3])=O.[Na+].C(O)=O.[CH3:8][C@H:9]1[CH2:18][NH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[CH:15]=2)[N:10]1[C:29](=[O:31])[CH3:30]>>[C:29]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[N:17]([CH:1]=[O:3])[CH2:18][C@@H:9]1[CH3:8])(=[O:31])[CH3:30]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 2723810Sodium FormateHCID 118078872HCID 118078872, compound

Product 1

HCID 118079019(S)-4-acetyl-3-methyl-7-(4-(methylsulfonyl)phenyl)-3,4-dihydroquinoxaline-1 (2H)-carbaldehydeYield 46%

Procedure

Sodium formate (14 mg, 0.200 mmol) and formic acid (46 mg, 1.0 mmol) were added to (S)-1-(2-methyl-6-(4-(methylsulfonyl)phenyl)-3,4-dihydroquinoxaline-1(2H)-yl)ethanone (0.2 M in 1,2-dichloroethane, 0.1 mL, 0.02 mmol) and shaken at room temperature for 5 h. The reaction was concentrated and the crude product was purified by mass-triggered preparatory HPLC. The product-containing fractions were combined and concentrated to afford (S)-4-acetyl-3-methyl-7-(4-(methylsulfonyl)phenyl)-3,4-dihydroquinoxaline-1 (2H)-carbaldehyde (0.0034 g, 46%). MS (ESI, pos. ion) m/z 373

Workup

  1. concentrationThe reaction was concentrated
  2. customthe crude product was purified by mass-triggered preparatory HPLC
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0d246a2c72af4094a08fbdaddd45726a
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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