Water → 4-Ethyl-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

HRID 498040Notes

Reaction equation

HRID 498040 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:3]=12.[CH2:22]([Mg]Br)[CH3:23].C(OCC)C.O>O1CCCC1>[CH2:22]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:3]=12)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 223201094-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolineHCID 178418443HCID 178418443, compound

Product 1

HCID 223202994-Ethyl-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolineYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (2.95 g, 10.0 mmol) in tetrahydrofuran (100 mL), a solution of 3M ethylmagnesium bromide in diethyl ether (4.00 mL, 12.0 mmol) was added dropwise under an argon atmosphere, and the solution was stirred at the same temperature for 1 hour. The reaction mixture was poured into iced water, and the organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvents were evaporated under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography (hexane:ethyl acetate=2:1) to give the title compound (0.33 g, 11% yield).

Workup

  1. extractionthe organic matter was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvents were evaporated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by basic silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ef2c796a556e43ef810e0807f1c87761
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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