Ethyl bromoacetate → (2-Methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-acetic acid ethyl ester

HRID 2415493Notes

Reaction equation

HRID 2415493 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([OH:17])=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C([O-])(O)=O.[Na+]>CN(C)C=O>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][O:17][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:11][C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1)[CH3:26]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 1358041182-Methyl-4-pyrrolidin-1-yl-quinolin-7-ol

Product 1

HCID 69287154(2-Methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-acetic acid ethyl esterYield 60,154.102%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 2-methyl-4-pyrrolidin-1-yl-quinolin-7-ol (797 mg, 3.49 mmol) in dimethylformamide (13 mL) was added sodium hydride (ca. 60% in oil, 168 mg, 4.19 mmol). After 30 min at 0° C., ethyl bromoacetate (0.5 mL, 4.50 mmol) was injected. After 2 h30, an aqueous solution of NaHCO3 was added and the aqueous layer was extracted with dichloromethane. The combined organic phases were washed with brine and water and then dried over sodium sulfate. After filtration, solvents were removed in a high vacuum. The brown oil was triturated with diethylether. After filtration, the solid was dried in a high vacuum to give 660 g (60.2%) of (2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-acetic acid ethyl ester as a light brown solid. ISP mass spectrum, m/e: 315.4 (M+1 calculated for C18H22N2O3: 315.4).

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. washThe combined organic phases were washed with brine and water
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration, solvents
  5. customwere removed in a high vacuum
  6. customThe brown oil was triturated with diethylether
  7. filtrationAfter filtration
  8. customthe solid was dried in a high vacuum

Sources & evidence

ORD record
ord-e488be2c7af4439795e63314090ce176
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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