Ethyl bromoacetate → 1-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2-ethoxycarbonylmethoxymethyl-3-hydroxymethyl-6,7-dimethoxynaphthalene

HRID 1740636Notes

Reaction equation

HRID 1740636 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:12]1[CH:17]=[C:16]([C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[CH:21]=[C:20]([CH2:32][OH:33])[C:19]=2[CH2:34][OH:35])[CH:15]=[CH:14][N:13]=1.[H-].[Na+].Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].[C:45]([O:48][CH2:49][CH3:50])(=[O:47])[CH3:46]>CN(C)C=O.O>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:12]1[CH:17]=[C:16]([C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[CH:21]=[C:20]([CH2:32][OH:33])[C:19]=2[CH2:34][O:35][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:15]=[CH:14][N:13]=1.[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:12]1[CH:17]=[C:16]([C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[CH:21]=[C:20]([CH2:32][O:33][CH2:46][C:45]([O:48][CH2:49][CH3:50])=[O:47])[C:19]=2[CH2:34][OH:35])[CH:15]=[CH:14][N:13]=1

Participants

8

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 99124671-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene

Product 2

HCID 220074271-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2-ethoxycarbonylmethoxymethyl-3-hydroxymethyl-6,7-dimethoxynaphthaleneHCID 220074351-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2-hydroxymethyl-3-ethoxycarbonylmethoxymethyl-6,7-dimethoxynaphthalene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[2-(2-oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (468 mg) in dimethylformamide (5 ml) is added sodium hydride (60 mg), and the mixture is stirred for 30 minutes. The mixture is cooled with ice, and thereto is added dropwise ethyl bromoacetate (0.17 ml), and the mixture is stirred overnight. To the residue are added ethyl acetate and water, and the ethyl acetate layer is separated, washed, dried and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform:acetone=5:1) to give 1-[2-(2-oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2-ethoxycarbonylmethoxymethyl-3-hydroxymethyl-6,7-dimethoxynaphthalene (70 mg, Example 96) and 1-[2-(2-oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2-hydroxymethyl-3-ethoxycarbonylmethoxymethyl-6,7-dimethoxynaphthalene (120 mg, Example 97), which are listed in Table 8.

Workup

  1. temperatureThe mixture is cooled with ice
  2. stirringthe mixture is stirred overnight
  3. customthe ethyl acetate layer is separated
  4. washwashed
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform:acetone=5:1)

Sources & evidence

ORD record
ord-b0db2ded5c13455e8148e687abcbf721
Source dataset
uspto-grants-1999_10
Patent number
US05969140

Reaction notes

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