4-Methoxybenzenesulfonyl chloride → HCID 11375051, compound

HRID 1431976Notes

Reaction equation

HRID 1431976 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[NH:10][CH:11]=2)[CH:2]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>CN(C=O)C.C1COCC1>[CH3:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([S:32]([N:10]2[CH:11]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:8]=[C:9]2[C:12]2[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=2)(=[O:34])=[O:33])=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 68615516HCID 68615516, compound

Product 1

HCID 11375051HCID 11375051, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(3-pyridyl)-2-(3,4,5-trimethoxyphenyl)-pyrrole (155 mg, 0.5 mmol, Example 76a) in dry DMF or THF (1.5 ml) NaH dispersion (48 mg, 2 equiv.) and p-methoxyphenylsulfonyl chloride (103 mg, 0.5 mmol) is added under a stream of nitrogen at 4° C. The reaction mixture is subsequently stirred for 12-18 h at room temperature and extracted with saturated aqueous NaHCO3 solution and ethyl acetate. The organic layer is dried and purified by flash chromatography and preparative HPLC. RT (program 1) 3.79. MS: 480.7.

Workup

  1. extractionextracted with saturated aqueous NaHCO3 solution and ethyl acetate
  2. customThe organic layer is dried
  3. custompurified by flash chromatography and preparative HPLC
  4. customRT (program 1) 3.79

Sources & evidence

ORD record
ord-7c0fe36ce25e4655a0648a9964e3d347
Source dataset
uspto-grants-2009_11
Patent number
US07612064B2

Reaction notes

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