Benzyloxyacetyl chloride → 1-(2-benzyloxyacetyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one

HRID 68173Notes

Reaction equation

HRID 68173 reaction equation
[CH2:1]([O:8][CH2:9][C:10](Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si]([O:20][C:21]1[C:30]2[C:25](=[C:26]([O:32][CH2:33][CH2:34][CH3:35])[CH:27]=[CH:28][C:29]=2[F:31])[N:24]=[CH:23][C:22]=1[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)(C(C)(C)C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][CH2:9][C:10]([N:24]1[C:25]2[C:30](=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[O:32][CH2:33][CH2:34][CH3:35])[C:21](=[O:20])[C:22]([C:36]2[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=2)=[CH:23]1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 177085Benzyloxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 674170464-(Tert-butyldimethylsilyloxy)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-quinolin

Product 1

HCID 584923631-(2-benzyloxyacetyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-oneYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyloxyacetyl chloride (1.9 ml, 3 equivalent weight) was added to a dichloromethane solution (50 ml) of 4-(tert-butyldimethylsilyloxy)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-quinolin (1.5 g, 3.4 mmol) while ice-cooling and the mixture was stirred overnight at room temperature. An aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction using ethyl acetate. The thus-obtained organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (n-hexane:ethyl acetate=2:1). The purified product was concentrated under reduced pressure, giving a colorless oily substance of 1-(2-benzyloxyacetyl)-5-fluoro -3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (250 mg, yield: 15%).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction
  3. dry with materialThe thus-obtained organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified
  6. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-72e64c8d365e48549dc92681a5cbe5fa
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

Loading…