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2-Bromo-4-fluorobenzene-1-sulfonyl chloride → methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate

HRID 715954
ノート
印刷プレビュー

反応式

HRID 715954 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH2:13][C:6]3=[CH:5][C:4]=2[C:3]=1[C:14]([O:16][CH3:17])=[O:15].[Br:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1.C(Cl)Cl.C(OCC)(=O)C>[Br:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[S:26]([NH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH2:13][C:6]3=[CH:5][C:4]=2[C:3]=1[C:14]([O:16][CH3:17])=[O:15])(=[O:28])=[O:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chlorideHCID 86712114methyl 7-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate2 回

生成物 1

HCID 70984190methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate収率 57.5%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 6344
Dichloromethane
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of methyl 7-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (Intermediate 18, 0.300 g) and 2-bromo-4-fluorobenzenesulfonyl chloride (0.427 g) in pyridine (4 mL) and DCM (12 mL) was stirred at room temperature for 30 minutes. The resultant mixture was diluted with ethyl acetate and washed with aqueous potassium carbonate solution (10%) and brine. The organic layer was dried (MgSO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-2% to give methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (0.350 g) as a white foam.

後処理

  1. washwashed with aqueous potassium carbonate solution (10%) and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by chromatography on silica
  6. washeluting with a mixture of methanol and DCM with a gradient of 0-2%

出典と根拠

ORDレコード
ord-e0f95ff4f32748d1b080749324e43240
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09187494B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート