Potassium Iodide → HCID 67395914, compound

HRID 1426721Notes

Reaction equation

HRID 1426721 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([S:9]([N:12]2[C:16]([C:17]3[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=3)=[C:15]([F:24])[C:14]([CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:13]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[CH3:35][S-:36].[Na+].[I-].[K+].CN(C)C=O>O1CCCC1.O>[F:24][C:15]1[C:14]([CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[CH:13][N:12]([S:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][S:36][CH3:35])[CH:4]=2)(=[O:11])=[O:10])[C:16]=1[C:17]1[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 67396174HCID 67396174, compound

Product 1

HCID 67395914HCID 67395914, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl {[1-{[3-(chloromethyl)phenyl]sulfonyl}-4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate (386 mg) in tetrahydrofuran (3 mL) were added sodium thiomethoxide (58 mg) and potassium iodide (125 mg) and the mixture was stirred for 21 hr. Dimethylformamide (3 mL) was added and the mixture was stirred at 100° C. for 76 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as a yellow oil (yield 291 mg, 74%).

Workup

  1. stirringthe mixture was stirred at 100° C. for 76 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionThe separated aqueous layer was extracted again with ethyl acetate
  4. washThe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-49372c56f927455fb73f2b0d1252695c
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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