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2-Bromo-4-fluorobenzene-1-sulfonyl chloride → methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-8-carboxylate

HRID 715964
ノート
印刷プレビュー

反応式

HRID 715964 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][CH:6]3[CH2:5][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][CH:6]3[CH2:5][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 86712116methyl 7-amino-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-8-carboxylate2 回

生成物 1

HCID 70984706methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-8-carboxylate収率 39.2%

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-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (Intermediate 29, 0.400 g) and 2-bromo-4-fluorobenzenesulfonyl chloride (0.565 g) in pyridine (4 mL) and DCM (12 mL) was stirred at room temperature for 30 minutes. The mixture was diluted with ethyl acetate and washed with aqueous potassium carbonate solution (10%) and brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM, with a gradient of 0-2%. The resultant solid was re-purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, containing 1% triethylamine, with a gradient of 0-100% to give a yellow solid which was again purified by chromatography on silica, eluting with a mixture of DCM and cyclohexane (50%), followed by DCM (100%). The resultant solid was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 5-30%, to give methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (0.317 g) as a yellow gum.

後処理

  1. washwashed with aqueous potassium carbonate solution (10%) and brine
  2. dry with materialdried (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%
  7. customThe resultant solid was re-purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane
  9. additioncontaining 1% triethylamine
  10. customwith a gradient of 0-100% to give a yellow solid which
  11. customwas again purified by chromatography on silica
  12. washeluting with a mixture of DCM and cyclohexane (50%)
  13. customThe resultant solid was purified by chromatography on silica
  14. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 5-30%

出典と根拠

ORDレコード
ord-0d7b174cfff2448ba8929fc4267ddf0b
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

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