Benzenesulfonyl chloride → HCID 67397692, compound

HRID 1426697Notes

Reaction equation

HRID 1426697 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]([CH2:14][C:15]1[C:19]([F:20])=[C:18]([C:21]2[C:22]([F:27])=[N:23][CH:24]=[CH:25][CH:26]=2)[NH:17][CH:16]=1)[CH3:13].[H-].[Na+].C1OCCOCCOCCOCCOC1.[C:45]1([S:51](Cl)(=[O:53])=[O:52])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[Cl-].[NH4+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]([CH2:14][C:15]1[C:19]([F:20])=[C:18]([C:21]2[C:22]([F:27])=[N:23][CH:24]=[CH:25][CH:26]=2)[N:17]([S:51]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)(=[O:53])=[O:52])[CH:16]=1)[CH3:13]

Participants

8

Reactant 5

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 3633615-Crown-5HCID 67396635HCID 67396635, compound

Product 1

HCID 67397692HCID 67397692, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2,4-dimethoxyphenyl)-N-{[4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}-N-methylmethanamine (2.98 g) in tetrahydrofuran (20 mL) was added sodium hydride (60% in oil, 421 mg) under ice-cooling. After stirring at the same temperature for 30 min, 15-crown-5 (1.80 mL) was added dropwise. After further stirring for 15 min, benzenesulfonyl chloride (1.15 mL) was added dropwise. After stirring for 1 hr at the same temperature, saturated aqueous ammonium chloride solution and water were added, and the mixture was extracted with ethyl acetate. The extract 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→7:3) to give the title compound as a yellow oil (yield 2.95 g, 72%).

Workup

  1. temperaturecooling
  2. stirringAfter further stirring for 15 min
  3. additionwere added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (eluent: hexane:ethyl acetate=9:1→7:3)

Sources & evidence

ORD record
ord-de6a5086359746faa6a90d8ee5c41f42
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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