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

HRID 29049

반응식

HRID 29049 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e856ec518eca4dabaf48ed51495e8a8b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420061B2

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