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Sodium hydride → 4-allyl-5-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 576520
ノート
印刷プレビュー

反応式

HRID 576520 の反応式
[H-].[Na+].[CH2:3]([C:6]1([CH3:21])[C:11]2[NH:12][C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][C:18]=3[C:10]=2[CH2:9][N:8]([CH3:20])[CH2:7]1)[CH:4]=[CH2:5].Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)=[CH2:25]>CN(C=O)C>[CH2:3]([C:6]1([CH3:21])[C:11]2[N:12]([CH2:25][C:24]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[CH2:23])[C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][C:18]=3[C:10]=2[CH2:9][N:8]([CH3:20])[CH2:7]1)[CH:4]=[CH2:5]
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

5

反応物 3

HCID 24758Sodium hydrideHCID 116942121-(3-Bromoprop-1-en-2-yl)-4-fluorobenzeneHCID 673559434-allyl-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

生成物 1

HCID 673564374-allyl-5-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole収率 35.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒
2 回

反応条件

温度
0 °C

実験手順

To a stirred suspension of sodium hydride (0.236 g, 5.9 mmol) in dry DMF (5 mL) at 0° C. was added 4-allyl-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1 g, 3.937 mol, in dry DMF 2 mL). After addition was complete, reaction mixture was stirred at 0° C. for an additional 10 min. 1-(1-Bromomethyl-vinyl)-4-fluoro-benzene (1.09 g, 5.118 mmol) in dry DMF (3 mL) was added dropwise at 0° C. The reaction mixture was stirred at 25° C. for 16 h. The reaction mixture was diluted with ice-water and extracted with EtOAc (2×50 mL). The organic layer was repeatedly washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure and the residue purified by chromatography on neutral aluminum oxide (eluting with EtOAc:Hexanes, 1:99) to obtain 700 mg of 4-allyl-5-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

後処理

  1. additionAfter addition
  2. customreaction mixture
  3. stirringThe reaction mixture was stirred at 25° C. for 16 h
  4. extractionextracted with EtOAc (2×50 mL)
  5. washThe organic layer was repeatedly washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue purified by chromatography on neutral aluminum oxide (eluting with EtOAc:Hexanes, 1:99)

出典と根拠

ORDレコード
ord-15e55457ec0a4b9dbf42cab2c48d1638
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040519B2

反応ノート

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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