Methyl iodide → HCID 59004250, compound

HRID 2242178Notes

Reaction equation

HRID 2242178 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[C:15]([CH3:19])[CH:14]=[CH:13][C:12]=3[NH:11][C:10](=[O:20])[C:9]=2[CH:8]=[N:7]1)[CH3:2].CI.[C:24]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[C:15]([CH3:19])[CH:14]=[CH:13][C:12]=3[N:11]([CH3:24])[C:10](=[O:20])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 135996471HCID 135996471, compound

Product 1

HCID 59004250HCID 59004250, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(8-Methyl-4-oxo-4,5-dihydro-pyrazolo[4,3-c]quinolin-1-yl)-acetic acid ethyl ester m (285 mg, 1 mmol), methyl iodide (142 mg, 1 mmol) and Cs2CO3 (650 mg, 2 mmol) were combined in dry DMF (4 mL) and the resultant mixture was heated at 40° C. for 8 h. The reaction mixture was cooled, diluted with water and extracted with ethyl acetate (2×20 mL) and the combined organic extract was dried over Na2SO4, and concentrated in vacuo. The crude residue was purified by column chromatography to provide the desired compound n (80% yield): LC MS (Method B): 300 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. extractionthe combined organic extract
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-3d4a48c7aa6a448aa4bc17cf63a9adf1
Source dataset
uspto-grants-2010_03
Patent number
US07671069B2

Reaction notes

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