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Methyl chloroformate → methyl 7-[N-(2-bromo-4-fluorobenzenesulfonyl)-N-(methoxy-carbonyl)amino]-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylate

HRID 927913
ノート
印刷プレビュー

反応式

HRID 927913 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]2[C:16]([C:17]3[CH2:29][CH2:28][O:27][C:18]=3[CH:19]=[N:20]2)=[CH:15][CH:14]=1)(=[O:11])=[O:10].[H-].[Na+].[H][H].Cl[C:35]([O:37][CH3:38])=[O:36]>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([N:12]([C:13]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]2[C:16]([C:17]3[CH2:29][CH2:28][O:27][C:18]=3[CH:19]=[N:20]2)=[CH:15][CH:14]=1)[C:35]([O:37][CH3:38])=[O:36])(=[O:10])=[O:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 71006928Methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-1,2-dihydro-furo[2,3-c]quinoline-6-carboxylate2 回HCID 178418361HCID 178418361、化合物

生成物 1

HCID 71006926methyl 7-[N-(2-bromo-4-fluorobenzenesulfonyl)-N-(methoxy-carbonyl)amino]-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylate収率 92.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-1,2-dihydro-furo[2,3-c]quinoline-6-carboxylate (Intermediate 22, 0.29 g) in THF (5 mL) was added slowly to a suspension of sodium hydride (40% oil dispersion, 0.048 g) in THF (15 mL). Once the evolution of hydrogen had ceased, methyl chloroformate (0.147 g) was added and the mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate solution, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with a mixture of ether and cyclohexane (1:1) and the solid was collected by filtration to give methyl 7-[N-(2-bromo-4-fluorobenzenesulfonyl)-N-(methoxy-carbonyl)amino]-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylate (0.3 g) as a pale orange solid.

後処理

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was triturated with a mixture of ether and cyclohexane (1:1)
  6. filtrationthe solid was collected by filtration

出典と根拠

ORDレコード
ord-5ca0c2f307d54be1947f9fc544b3e0e0
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09290472B2

反応ノート

読み込み中…

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