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

HRID 715957ノート

反応式

HRID 715957 の反応式
[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]

参加物

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 70983888methyl 2-(3-hydroxypropyl)-5-nitro-1H-indole-4-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-acc6923098c046a89520401d6a440795
出典データセット
uspto-grants-2015_11
特許番号
US09187494B2

反応ノート

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