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

HRID 29049

反応式

HRID 29049 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e856ec518eca4dabaf48ed51495e8a8b
出典データセット
uspto-grants-2008_09
特許番号
US07420061B2

関連ノート

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