Pyridine → 1-Methyl-4-bromoacetyl-5-(2-fluorobenzoyl)-1,2,3,4-tetrahydroquinoxaline

HRID 1109721Notes

Reaction equation

HRID 1109721 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[C:7]([C:12](=[O:20])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[CH:8]=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.N1C=CC=CC=1.[Br:27][CH2:28][C:29](Br)=[O:30]>C(Cl)Cl>[CH3:1][N:2]1[C:11]2[C:6](=[C:7]([C:12](=[O:20])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[CH:8]=[CH:9][CH:10]=2)[N:5]([C:29](=[O:30])[CH2:28][Br:27])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 102651411-Methyl-5-(2-fluorobenzoyl)-1,2,3,4-tetrahydroquinoxaline

Product 1

HCID 104755351-Methyl-4-bromoacetyl-5-(2-fluorobenzoyl)-1,2,3,4-tetrahydroquinoxaline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-methyl-5-(2-fluorobenzoyl)-1,2,3,4-tetrahydroquinoxaline (11.99 g) and pyridine (4.04 g) in methylene chloride (200 ml) was dropwise added a solution of bromoacetyl bromide (5.09 ml) in methylene chloride (10 ml) under stirring at a temperature below 10° C. and the mixture was stirred for 3 hours at the same temperature. The reaction mixture was washed with water twice and dried. Removal of the solvent afforded viscous oil. The viscous oil was triturated with diisopropyl ether, collected by filtration, washed with diisopropyl ether and dried to give 1-methyl-4-bromoacetyl-5-(2-fluorobenzoyl)-1,2,3,4-tetrahydroquinoxaline (17.18 g).

Workup

  1. stirringthe mixture was stirred for 3 hours at the same temperature
  2. washThe reaction mixture was washed with water twice
  3. customdried
  4. customRemoval of the solvent
  5. customafforded viscous oil
  6. customThe viscous oil was triturated with diisopropyl ether
  7. filtrationcollected by filtration
  8. washwashed with diisopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-2d578288fbab40fdaa93168904260457
Source dataset
uspto-grants-1994_06
Patent number
US05322842

Reaction notes

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