Water → N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3-fluorophenyl]methanesulfonamide

HRID 1591823노트

반응식

HRID 1591823 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[C:4]([F:16])[CH:3]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].O>N1C=CC=CC=1.C(OCC)(=O)C>[C:14]([C:11]1[N:12]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:3][C:4]=2[F:16])=[CH:9][CH:10]=1)#[N:15]

참가 물질

6

반응물 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 160504325-(4-amino-2-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

생성물 1

HCID 16051367N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3-fluorophenyl]methanesulfonamide수율 68.2%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

5-(4-amino-2-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (0.20 g, 0.93 mmol) was dissolved in pyridine (2.0 mL). Methanesulfonyl chloride (0.07 mL, 0.9 mmol) was added and the mixture was stirred for 16 hours, followed by the addition of water. The mixture was diluted with ethyl acetate and then was washed with water, saturated CuSO4, 2N HCl, brine, dried over MgSO4, and concentrated. The crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-50% ethyl acetate in hexane) to afford 0.18 g of N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3-fluorophenyl]methanesulfonamide.

후처리

  1. washwas washed with water, saturated CuSO4, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-50% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-6d57220428844858a634e9d48cc56d37
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291643B2

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