Ethyl bromoacetate → HCID 69652382, compound

HRID 2212204Notes

Reaction equation

HRID 2212204 reaction equation
I.[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1.[CH2:24]([O:26][C:27](=[O:30])[CH2:28]Br)[CH3:25].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH2:24]([O:26][C:27](=[O:30])[CH2:28][N:15]1[CH2:16][CH2:17][CH2:18][CH:13]([N:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:3]([Cl:2])[C:4]=3[C:5]3=[N:22][O:21][C:20]([CH3:23])=[C:6]3[C:7]2=[O:19])[CH2:14]1)[CH3:25]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

Product 1

HCID 69652382HCID 69652382, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 9-chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide (446 mg, 1.0 mmol) in tetrahydrofuran (20 mL) add ethylbromoacetate (0.11 mL, 1.0 mmol) and follow by potassium carbonate (346 mg, 2.5 mmol). Stir the mixture at room temperature under nitrogen overnight. Concentrate the mixture, partition between water and 20% isopropanol/chloroform, and separate. Wash the organic layer with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–1% methanol/chloroform) to give 261 mg of the title compound as a clear oil, 65% yield. 1H NMR: consistent with structure. MS (ion spray) 404 (M+).

Workup

  1. concentrationConcentrate the mixture
  2. custompartition between water and 20% isopropanol/chloroform
  3. customseparate
  4. washWash the organic layer with saturated aqueous sodium bicarbonate solution, brine
  5. dry with materialdry over magnesium sulfate
  6. concentrationconcentrate
  7. customPurify by flash chromatography on silica gel (eluting with 0–1% methanol/chloroform)

Sources & evidence

ORD record
ord-93c747a56e33433683c1dce40f3b77ca
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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