N-(4-bromophenyl)-N-methylbenzenesulfonamide → N-(4-{1-[1-(2-Ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-hydroxyethyl}-phenyl)-N-methyl-benzenesulfonamide

HRID 1791019Notes

Reaction equation

HRID 1791019 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:18])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[Li]C(C)(C)C.[CH2:24]([O:26][CH2:27][CH2:28][N:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH3:25]>CCOCC.CCCCC.C1COCC1>[CH2:24]([O:26][CH2:27][CH2:28][N:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:18])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1)([OH:39])[C:35]([F:36])([F:37])[F:38])[CH3:25]

Participants

7

Reactant 3

HCID 5171346N-(4-bromophenyl)-N-methylbenzenesulfonamideHCID 68869870N-ethoxyethyl-2-trifluoroacetylpyrroleHCID 178418306HCID 178418306, compound

Product 1

HCID 21943462N-(4-{1-[1-(2-Ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-hydroxyethyl}-phenyl)-N-methyl-benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 75 mg (0.23 mmol) of N-(4-bromophenyl)-N-methyl-benzenesulfonamide in 4 mL of Et2O at −78° C. was added dropwise 285 μL (0.49 mmol) of a 1.7 M solution of tert-BuLi in pentane and the resultant mixture was stirred at −78° C. for 10 min. To this mixture was then added a solution of 81 mg (0.34 mmol) of N-ethoxyethyl-2-trifluoroacetylpyrrole in 3 mL THF and the mixture was allowed to gradually warm to room temperature over an 18 h period. The reaction mixture was quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (hexanes:EtOAc, 4:1) to give the title compound.

Workup

  1. customThe reaction mixture was quenched by the addition of a saturated aqueous solution of ammonium chloride
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography on silica gel (hexanes:EtOAc, 4:1)

Sources & evidence

ORD record
ord-cbf5c4679a00474b8f5f7f699350d347
Source dataset
uspto-grants-2006_07
Patent number
US07071358B2

Reaction notes

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