Ethyl 2-bromopropionate → HCID 19365526, compound

HRID 849944Notes

Reaction equation

HRID 849944 reaction equation
[NH2:1][C:2]1[C:3]([Cl:21])=[CH:4][C:5]([Cl:20])=[C:6]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:13]=2)[CH:7]=1.Br[CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>O>[Cl:20][C:5]1[CH:4]=[C:3]([Cl:21])[C:2]([NH:1][CH:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:29])=[CH:7][C:6]=1[C:8]1[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 79040Ethyl 2-bromopropionateHCID 19365503HCID 19365503, compound2×

Product 1

HCID 19365526HCID 19365526, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 0.15 g of 3-(5-amino-2,4-dichlorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-334) and 172 μl of ethyl 2-bromopropionate was stirred at 150° C. for 3 hours. After completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 92 mg (yield, 48%) of 3-{2,4-dichloro-5-[1-(ethoxycarbonyl)ethylamino]phenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-336).

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-06425866121548309d27122d3d328c33
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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