4-Fluoroaniline → 1-(4-Fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)pyrrole

HRID 1585056노트

반응식

HRID 1585056 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH2:13][C:14](=O)[CH3:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)=[CH:12][CH:13]=[C:14]2[CH3:15])=[CH:21][CH:20]=1

참가 물질

5

반응물 2

HCID 97314-FluoroanilineHCID 105388711-[4-(Methylsulfonyl)phenyl]-1,4-pentanedione

생성물 1

HCID 27657241-(4-Fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)pyrrole수율 79.2%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

실험 절차

A mixture of 1-(4-methylsulfonylphenyl)-1,4-pentanedione (580 mg, 2.28 mmol) of Step 2, 4-fluoroaniline (0.24 ml, 2.5 mmol) and p-toluenesulfonic acid (30 mg) in toluene (50 ml) was heated to reflux for 20 hours. The reaction mixture was cooled, filtered and concentrated. The crude mixture (820 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3) to give 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl)-1H-pyrrole (595 mg, 79%) as a white solid: mp (DSC) 157° C. Anal Calc'd. for C18H16NSO2F: C, 65.64; H, 4.90; N, 4.25; S, 9.73. Found: C, 65.44; H, 5.05; N, 4.16; S, 9.90.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude mixture (820 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 7/3)

출처 및 근거

ORD 기록
ord-f7e49e5e94fc40d2a5be01c6b594bd3b
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05935990

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