Water → HCID 57803044, compound

HRID 2102699Notes

Reaction equation

HRID 2102699 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[H-].[Li+].Cl[C:15]1[N:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([O:23][CH3:24])[CH:16]=1.O>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:15]3[CH:16]=[C:17]([O:23][CH3:24])[N:18]=[C:19]([O:21][CH3:22])[N:20]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62714Lithium hydrideHCID 806004-Chloro-2,6-dimethoxypyrimidineHCID 7363446-Chloro-1,3-dihydroindol-2-one

Product 1

HCID 57803044HCID 57803044, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 6-chlorooxindole (0.94 g, 5.34 mmol) (Cresent Chem.) in N,N-dimethylformamide (20 mL) at room temperature was added lithium hydride (86 mg, 10.7 mmol) (Aldrich). The mixture was stirred at room temperature for 10 minutes, then 6-chloro-2,4-dimethoxy-pyrimidine (0.93 g, 5.34 mmol) (Aldrich) was added. The reaction mixture was heated at 110° C. for 3 hours. The mixture was cooled to room temperature. Water (100 mL) was added, and mixture was extracted with ethyl acetate (2×100 mL). The organic layers were separated, combined, washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography (ethyl acetate) to give rac-6-chloro-3-(2,6-dimethoxy-pyrimidin-4-yl)-1,3-dihydro-indol-2-one as a brown solid. (Yield 0.23 g, 14%).

Workup

  1. temperatureThe reaction mixture was heated at 110° C. for 3 hours
  2. temperatureThe mixture was cooled to room temperature
  3. extractionmixture was extracted with ethyl acetate (2×100 mL)
  4. customThe organic layers were separated
  5. washwashed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-4481670591ff43658afb3d970e57db57
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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