Ethyl 2-bromopropionate → HCID 19365522, compound

HRID 849939Notes

Reaction equation

HRID 849939 reaction equation
[NH2:1][C:2]1[C:3]([F:20])=[CH:4][CH:5]=[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:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24]>O>[CH2:26]([O:25][C:23]([CH:22]([NH:1][C:2]1[C:3]([F:20])=[CH:4][CH:5]=[C:6]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:16])([F:17])[F:15])=[CH:12][N:13]=2)[CH:7]=1)[CH3:28])=[O:24])[CH3:27]

Participants

4

Reactant 2

HCID 79040Ethyl 2-bromopropionateHCID 19365514HCID 19365514, compound2×

Product 1

HCID 19365522HCID 19365522, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.12 g of 3-(5-amino-4-fluorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-19) and 0.23 g of ethyl 2-bromopropionate was stirred at 130° 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 52 mg (yield, 32%) of 3-{5-[1-(ethoxycarbonyl)ethylamino]-4-fluorophenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-355; m.p., 78.2° C.).

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-d83f0ac1f0c9476f859ad6f92b7614fa
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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