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2-Bromo-4-fluorobenzene-1-sulfonyl chloride → Methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-furo[2,3-c]quinoline-6-carboxylate

HRID 1778337
ノート
印刷プレビュー

反応式

HRID 1778337 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[NH2:13][C:14]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]2[C:17]([C:18]3[CH:30]=[CH:29][O:28][C:19]=3[CH:20]=[N:21]2)=[CH:16][CH:15]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:13][C:14]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]2[C:17]([C:18]3[CH:30]=[CH:29][O:28][C:19]=3[CH:20]=[N:21]2)=[CH:16][CH:15]=1)(=[O:11])=[O:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chloride2 回HCID 66685912Methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate2 回

生成物 1

HCID 66685289Methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-furo[2,3-c]quinoline-6-carboxylate収率 24.5%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

反応条件

温度
70 °C

実験手順

A solution of 2-bromo-4-fluorobenzenesulfonyl chloride (0.57 g) in pyridine (10 mL) was heated to 70° C. and a solution of methyl 7-amino-furo[2,3-c]quinoline-6-carboxylate (Intermediate 16, 0.33 g) in pyridine (10 mL) was added. The mixture was stirred and heated at 70° C. for 4 hours. Further 2-bromo-4-fluorobenzenesulfonyl chloride (0.57 g) was added and the mixture was stirred and heated at 70° C. overnight. After cooling, the mixture was filtered and the solid was washed with methanol. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-60%. The product was triturated with diethyl ether and the solid was collected by filtration to give methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-furo[2,3-c]quinoline-6-carboxylate (0.16 g) as a yellow solid.

後処理

  1. stirringthe mixture was stirred
  2. temperatureheated at 70° C. overnight
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. washthe solid was washed with methanol
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-60%
  9. customThe product was triturated with diethyl ether
  10. filtrationthe solid was collected by filtration

出典と根拠

ORDレコード
ord-5687ad9c6ba94877852d1ea388dc9d65
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266896B2

反応ノート

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