Methyl 3,3,3-trifluoro-2-oxopropanoate → HCID 89783720, compound

HRID 1056046Notes

Reaction equation

HRID 1056046 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[F:10][C:11]([F:19])([F:18])[C:12](=O)[C:13](OC)=[O:14]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:9][C:13](=[O:14])[C:12]([C:11]([F:19])([F:18])[F:10])=[N:8]2

Participants

4

Reactant 2

HCID 2734931Methyl 3,3,3-trifluoro-2-oxopropanoateHCID 124898393-Bromobenzene-1,2-diamine

Product 1

HCID 89783720HCID 89783720, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-bromobenzene-1,2-diamine (1.00 g, 5.35 mmol, CombiBlocks, Inc., San Diego, Calif.) and methyl 3,3,3-trifluoro-2-oxopropanoate (0.655 mL, 6.42 mmol; Alfa Aesar, Ward Hill, Mass.) in EtOH (15 mL) was stirred at reflux under argon for 17 h. The mixture was concentrated in vacuo. Purification by silica gel (0-70% EtOAc/Hexanes) provided 8-bromo-3-(trifluoromethyl)quinoxalin-2(1H)-one (224b, 29% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.43 (1H, br. s.), 8.04 (1H, d, J=7.8 Hz), 7.95 (1H, d, J=8.2 Hz), 7.38 (1H, t, J=7.9 Hz). 19F NMR (377 MHz, DMSO-d6) δ ppm −68.44 (3F, br. s.). MS (ESI, pos. ion) m/z: 293.0 (M+1).

Workup

  1. temperatureat reflux under argon for 17 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customPurification by silica gel (0-70% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-e0381781d249446fb69b1f577ebd10e7
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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