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4-Toluenesulfonyl chloride → tert-butyl 7-bromo-9-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

HRID 1020638
ノート
印刷プレビュー

反応式

HRID 1020638 の反応式
[OH-].[Na+].[S:3](Cl)([C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[Br:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][C:20]=3[NH:21]2)=[CH:17][CH:16]=1.CCOC(C)=O>O.C1(C)C=CC=CC=1>[Br:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][C:20]=3[N:21]2[S:3]([C:6]2[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=2)(=[O:5])=[O:4])=[CH:17][CH:16]=1
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

7

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19605584tert-Butyl 7-bromo-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

生成物 1

HCID 57950467tert-butyl 7-bromo-9-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate収率 90.2%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
2 回
HCID 1140Toluene溶媒

反応条件

温度
25 °C

実験手順

6 N NaOH solution (6 mL), (Bu4N)2SO4 (50% wt. solution in H2O, 0.20 mL), and TsCl (646 mg, 3.39 mmol) were added to a suspension of tert-butyl 7-bromo-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (991 mg, 2.82 mmol) in toluene (20 mL) and the resulting suspension was stirred at 25° C. for 1.5 h. H2O and EtOAc were added to the suspension and the phases were separated. The organic phase was washed with H2O, dried over Na2SO4 and concentrated under reduced pressure to afford the title compound (1.285 g, 90%) as a white foam: 1H NMR (300 MHz, CDCl3) δ 8.32 (d, J=1.5 Hz, 1H), 7.78-7.66 (m, 2H), 7.36 (dd, J=8.4, 1.5 Hz, 1H), 7.25-7.21 (m, 2H), 7.21-7.13 (m, 1H), 4.92-4.81 (m, 2H), 3.74-3.63 (m, 2H), 2.70-2.61 (m, 2H), 2.37 (s, 3H), 1.50 (s, 9H).

後処理

  1. customthe phases were separated
  2. washThe organic phase was washed with H2O
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-47e4517af6a949ac930163690762290d
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08716308B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート