p-Toluenesulfonic acid → 4-(2-(4-Fluorophenyl)-1H-pyrrol-1-yl)-N-methylbenzenesulfonamide

HRID 29049

Reaction equation

HRID 29049 reaction equation
CC1(C)CO[CH:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=O)OC1.[CH3:20][NH:21][S:22]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)(=[O:24])=[O:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]2[N:29]([C:28]3[CH:30]=[CH:31][C:25]([S:22]([NH:21][CH3:20])(=[O:24])=[O:23])=[CH:26][CH:27]=3)[CH:5]=[CH:8][CH:9]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 743684-amino-N-methylbenzene-1-sulfonamideHCID 106354633-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one

Product 1

HCID 105204474-(2-(4-Fluorophenyl)-1H-pyrrol-1-yl)-N-methylbenzenesulfonamideYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(5,5-dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one (Step 4) (400 mg, 1.5 mmol), 4-[(N-methylamino)sulfonyl]aniline (Step 6) (308 mg, 1.65 mmol) and p-toluenesulfonic acid (40 mg) in toluene (80 ml) was heated to reflux for 48 hr. The reaction mixture was cooled, filtered and concentrated. The crude yellowish solid (760 mg) was chromatographed (silica gel, hexane/ethyl acetate 7/3) to give 4-[2-(4-fluorophenyl)-1H-pyrrol-1-yl]-N-methylbenzenesulfonamide (198 mg, 40%) as a white solid: mp (DSC) 174° C. Anal Calc'd. for C17H15N2FO2S 0.25 H2O: C, 60.97; H, 4.67; N, 8.37. Found: C, 60.86; H, 4.56; N, 8.01.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 hr
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude yellowish solid (760 mg) was chromatographed (silica gel, hexane/ethyl acetate 7/3)

Sources & evidence

ORD record
ord-e856ec518eca4dabaf48ed51495e8a8b
Source dataset
uspto-grants-2008_09
Patent number
US07420061B2

Linked notes

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