Pyridine → HCID 118079639, compound

HRID 1485803Notes

Reaction equation

HRID 1485803 reaction equation
N1C=CC=CC=1.[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18](=[O:20])[CH3:19])[C@@H:13]([CH3:21])[CH2:12][NH:11]2.[Cl:22][C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[C:18]([N:14]1[C:15]2[C:10](=[CH:9][C:8]([Br:7])=[CH:17][CH:16]=2)[N:11]([C:23]([Cl:22])=[O:25])[CH2:12][C@@H:13]1[CH3:21])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 118078861(S)-1-(6-bromo-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)ethanone

Product 1

HCID 118079639HCID 118079639, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (0.150 mL, 1.86 mmol) was added to a solution of (S)-1-(6-bromo-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)ethanone (0.500 g, 1.86 mmol) in dichloromethane (6.6 mL). Triphosgene (0.197 g, 0.663 mmol) was then added in portions over ten minutes, and the reaction mixture stirred for 2 h at room temperature. The reaction was diluted with dichloromethane and washed with 1 N aqueous HCl solution. The organic phase was separated and washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and concentrated in a Genevac to afford (S)-4-acetyl-7-bromo-3-methyl-3,4-dihydroquinoxaline-1(2H)-carbonyl chloride, which was dissolved in 1,2-dichloroethane (9.0 mL) to afford a 0.2 M solution.

Workup

  1. washwashed with 1 N aqueous HCl solution
  2. customThe organic phase was separated
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in a Genevac

Sources & evidence

ORD record
ord-aba8f0ffd24c47dba8c34ed66350ebca
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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