Sodium Iodide → HCID 86762137, compound

HRID 2048009Notes

Reaction equation

HRID 2048009 reaction equation
[I-].[Na+].[H-].[Na+].[F:5][C:6]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH3:19])=[C:12]2[C:7]=1[C:8](=[O:28])[C:9]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[CH:10][NH:11]2.ClCOC(=O)[CH2:33][NH:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].[C:44](=[O:47])(O)[O-:45].[Na+].[CH3:49]N(C=O)C>>[C:44]([O:45][N:34]([CH2:33][N:11]1[C:12]2[C:7](=[C:6]([F:5])[CH:15]=[CH:14][C:13]=2[O:16][CH2:17][CH2:18][CH3:19])[C:8](=[O:28])[C:9]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)=[CH:10]1)[CH2:35][C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])(=[O:47])[CH3:49]

Participants

7

Reactant 6

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 251656785-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-oneHCID 89980727HCID 89980727, compound

Product 1

HCID 86762137HCID 86762137, compoundYield 18%

Procedure

Sodium iodide (1.4 g, 0.9 mmol) and sodium hydride (60% oil base, 220 mg, 5.5 mmol) were added to a DMF solution (15 ml) of 5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (1.0 g, 3.0 mmol) and stirred at room temperature for 10 minutes. Chloromethyl(tert-butoxycarbonylmethylamino)acetate (2.52 g, 10.6 mmol) was added to the reaction mixture while ice-cooling, and then the mixture was stirred at room temperature for 3 hours. An aqueous sodium bicarbonate solution was added to the reaction mixture and then the mixture was subjected to 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 material was concentrated to dryness under reduced pressure, giving a pale yellow amorphous solid of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-ylmethyl(tert-butoxycarbonyl methylamino) acetate (290 mg, yield: 18%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. extractionthe mixture was subjected to extraction
  4. dry with materialThe thus-obtained organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. concentrationThe purified material was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b63a540bb0be4cb19056c94eebcee036
Source dataset
uspto-grants-2013_11
Patent number
US08592593B2

Reaction notes

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