Sodium Iodide → HCID 57722476, compound

HRID 1931223Notes

Reaction equation

HRID 1931223 reaction equation
[I-].[Na+].Cl[Si](C)(C)[CH3:5].[CH2:8]([O:15][C:16]1[C:21]([C:22](=[O:32])[NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:20][N:19]=[C:18]([C:33]([O:35][CH3:36])=[O:34])[C:17]=1[O:37][CH3:38])[C:9]1C=CC=CC=1.S([O-])(O)=O.[Na+]>C(#N)C>[CH3:17][C:16]([CH3:21])=[O:15].[CH:16]([O:15][CH:8]([CH3:9])[CH3:5])([CH3:17])[CH3:21].[F:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][NH:23][C:22]([C:21]2[C:16](=[O:15])[C:17]([O:37][CH3:38])=[C:18]([C:33]([O:35][CH3:36])=[O:34])[NH:19][CH:20]=2)=[O:32])=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 23665763Sodium BisulfiteHCID 57722482HCID 57722482, compound

Product 2

HCID 22221350Acetone diisopropyl etherHCID 57722476HCID 57722476, compoundYield 253.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of sodium iodide (5.51 g, 36.8 mmol) in acetonitrile (50 ml) was added chlorotrimethylsilane (4.66 ml, 36.8 mmol), and the mixture was stirred at room temperature for 10 minutes. After to this solution was added the compound 27 (2.60 g, 6.13 mmol) under ice-cooling, this was stirred at the same temperature for 20 minutes. To the reaction solution was added a 5% sodium hydrogen sulfite solution, followed by extraction with ethyl acetate. The extract was washed with an aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chlorite solution, and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting solid matter was recrystallized to obtain (acetone-diisopropyl ether) and methyl 5-(4-fluorobenzylcarbamoyl)-3-methoxy-4-oxo-1,4-dihydropyridine-2-carboxylate 28 (1.73 g, 84%) as a colorless crystal.

Workup

  1. temperaturecooling
  2. stirringthis was stirred at the same temperature for 20 minutes
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with an aqueous saturated sodium bicarbonate solution
  5. dry with materialan aqueous saturated sodium chlorite solution, and dried with anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting solid matter was recrystallized

Sources & evidence

ORD record
ord-f5152a464b7246fb8827c0efaa685fbd
Source dataset
uspto-grants-2012_05
Patent number
US08188271B2

Reaction notes

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