Methanesulfonyl chloride → methyl 2-(3-methanesulfonyloxypropyl)-5-nitro-1H-indole-4-carboxylate

HRID 715957노트

반응식

HRID 715957 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][CH2:9][C:10]1[NH:11][C:12]2[CH:13]=[CH:14][C:15]([N+:23]([O-:25])=[O:24])=[C:16]([C:19]([O:21][CH3:22])=[O:20])[C:17]=2[CH:18]=1>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][CH2:9][C:10]1[NH:11][C:12]2[CH:13]=[CH:14][C:15]([N+:23]([O-:25])=[O:24])=[C:16]([C:19]([O:21][CH3:22])=[O:20])[C:17]=2[CH:18]=1)(=[O:4])=[O:3]

참가 물질

5

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 70983888methyl 2-(3-hydroxypropyl)-5-nitro-1H-indole-4-carboxylate2회

생성물 1

HCID 86712115methyl 2-(3-methanesulfonyloxypropyl)-5-nitro-1H-indole-4-carboxylate수율 99.8%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

Methanesulfonyl chloride (0.176 g) was added to a solution of methyl 2-(3-hydroxypropyl)-5-nitro-1H-indole-4-carboxylate (Intermediate 21, 0.360 g) in pyridine (1 mL) and DCM (10 mL) and the reaction mixture was stirred at room temperature for 4 hours. The mixture was diluted with DCM, washed with aqueous citric acid (5%), aqueous sodium bicarbonate and brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was dissolved in toluene and evaporated to dryness, four times to give methyl 2-(3-methanesulfonyloxypropyl)-5-nitro-1H-indole-4-carboxylate (0.460 g) as an orange gum.

후처리

  1. washwashed with aqueous citric acid (5%), aqueous sodium bicarbonate and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionthe residue was dissolved in toluene
  6. customevaporated to dryness, four times

출처 및 근거

ORD 기록
ord-acc6923098c046a89520401d6a440795
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187494B2

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