Sodium hydride → 4-chloro-5-(2-fluoropyridin-3-yl)-1-[(1-methyl-1H-pyrazol-4-yl)sulfonyl]-1H-pyrrole-3-carbaldehyde

HRID 1426730Notes

Reaction equation

HRID 1426730 reaction equation
[Cl:1][C:2]1[C:3]([CH:14]=[O:15])=[CH:4][NH:5][C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[CH3:33][N:34]1[CH:38]=[C:37]([S:39](Cl)(=[O:41])=[O:40])[CH:36]=[N:35]1>O1CCCC1.O>[Cl:1][C:2]1[C:3]([CH:14]=[O:15])=[CH:4][N:5]([S:39]([C:37]2[CH:36]=[N:35][N:34]([CH3:33])[CH:38]=2)(=[O:41])=[O:40])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 170247301-methyl-1H-pyrazole-4-sulfonyl chlorideHCID 866239794-chloro-5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 866239994-chloro-5-(2-fluoropyridin-3-yl)-1-[(1-methyl-1H-pyrazol-4-yl)sulfonyl]-1H-pyrrole-3-carbaldehydeYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (150 mg) in tetrahydrofuran (20 mL) was added sodium hydride (60% in oil, 81 mg) at room temperature and the mixture was stirred for 15 min. 15-Crown-5 (442 mg) was added dropwise and the mixture was stirred for 5 min. 1-methyl-1H-pyrazole-4-sulfonyl chloride (242 mg) was added and the mixture was further stirred for 30 min. The reaction mixture was diluted with water, and 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 silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:4) to give the title compound as a colorless oil (yield 160 mg, 65%).

Workup

  1. stirringthe mixture was stirred for 5 min
  2. stirringthe mixture was further stirred for 30 min
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:4)

Sources & evidence

ORD record
ord-a7b1ba0c498a4edb995b0549bc82c49c
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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