Benzyl Bromide → Ethyl 2-benzyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate

HRID 1842472Notes

Reaction equation

HRID 1842472 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=[C:3]12.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[CH2:22]([N:7]1[CH2:6][CH2:5][N:4]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=[C:3]2[C:2]1=[O:1])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 57517456Ethyl 1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate

Product 1

HCID 58465682Ethyl 2-benzyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate (29.8 mg, 0.143 mmol) in acetonitrile (1 mL) was added cesium carbonate (60.6 mg, 0.186 mmol) and benzyl bromide (36.7 mg, 0.215 mmol). The reaction mixture was heated at 70° C. overnight. Upon cooling to room temperature all insolubles were removed by filtration and the solvent evaporated to dryness to afforde crude Intermediate 34.

Workup

  1. temperatureUpon cooling to room temperature all insolubles
  2. customwere removed by filtration
  3. customthe solvent evaporated to dryness

Sources & evidence

ORD record
ord-3ae347480f1a4d2fbe888bedfcdf9c22
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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