Water → HCID 42629095, compound

HRID 254285Notes

Reaction equation

HRID 254285 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:12]([CH2:16][CH2:17][CH3:18])=[N:13][C:14]=2[CH3:15])[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C[Mg+].[Br-].[CH2:22](OCC)C.O>O1CCCC1>[CH3:15][C:14]1[N:13]=[C:12]([CH2:16][CH2:17][CH3:18])[N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:11]=[C:2]([CH3:22])[C:3]=12

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 86630792HCID 86630792, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 42629095HCID 42629095, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.6 g 4-Chloro-3-methyl-1-propyl-imidazo(1,5-a)quinoxaline (10 mmol) were dissolved in 50 ml tetrahydrofuran. At room temperature 12 ml 3 M MeMgBr solution in diethylether (36 mmol) was added, followed by 8 hours stirring. After complete reaction, controlled by TLC, 0.5 ml water were added and diethylether was distilled off. The residue was distributed between 100 ml dichloromethane, 25 ml water and 25 ml 10% aqueous ammonia. The organic layer was filtered off, and distilled to dryness. The residue (2.5 g) was chromatographed on silica gel with 5% MeOH/CH2Cl2.

Workup

  1. customAfter complete reaction
  2. additionwere added
  3. distillationdiethylether was distilled off
  4. filtrationThe organic layer was filtered off
  5. distillationdistilled to dryness
  6. customThe residue (2.5 g) was chromatographed on silica gel with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-83e1aedcca8b428b934c379e585d0e3f
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

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