Triethyl phosphite → 2-Ethoxycarbonyl-1-diethoxyphosphoryl-7-trifluoromethylimidazo[1,2-a]quinoxalin-4(5H)-one

HRID 1599433Notes

Reaction equation

HRID 1599433 reaction equation
BrC[C:3]1[N:7]2[C:8]3[C:13]([NH:14][C:15](=[O:16])[C:6]2=[N:5][C:4]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12][C:11]([C:17]([F:20])([F:19])[F:18])=[CH:10][CH:9]=3.[P:26]([O:33]CC)([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29]>>[CH2:24]([O:23][C:21]([C:4]1[N:5]=[C:6]2[C:15](=[O:16])[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:17]([F:20])([F:18])[F:19])[CH:12]=3)[N:7]2[C:3]=1[P:26]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:33])=[O:22])[CH3:25]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 18928128HCID 18928128, compound

Product 1

HCID 189281162-Ethoxycarbonyl-1-diethoxyphosphoryl-7-trifluoromethylimidazo[1,2-a]quinoxalin-4(5H)-oneYield 63%

Procedure

1-Bromomethyl-2-ethoxycarbonyl-7-trifluoromethylimidazo[1,2-a]quinoxalin-4(5H)-one (Example 3) (840 mg, 2.0 mmol) and triethyl phosphite (12 ml) was heated at 120° C. for 16 h. The mixture was concentrated in vacuo and the residue submitted to flash chromatography on silica gel, eluting with dichloromethane/methanol (9:1). The purified product was washed with ether to give 600 mg (63%) of the title compound. M.p. 198°-199° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washeluting with dichloromethane/methanol (9:1)
  3. washThe purified product was washed with ether

Sources & evidence

ORD record
ord-65ffd8ee1eb4413997b3efb29023e418
Source dataset
uspto-grants-1998_04
Patent number
US05741785

Reaction notes

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