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Sodium hydride → 4-((4-ethyl-1-methylpiperidin-4-yl)methoxy)-9H-diprido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60297
ノート
印刷プレビュー

反応式

HRID 60297 の反応式
[CH2:1]([C:3]1([CH2:10][OH:11])[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1)[CH3:2].[H-].[Na+].Cl[C:15]1[C:23]2[C:22]3[CH:24]=[C:25]([C:28]#[N:29])[N:26]=[CH:27][C:21]=3[N:20](COCC[Si](C)(C)C)[C:19]=2[N:18]=[CH:17][CH:16]=1>O1CCCC1.O.C(OCC)(=O)C>[CH2:1]([C:3]1([CH2:10][O:11][C:15]2[C:23]3[C:22]4[CH:24]=[C:25]([C:28]#[N:29])[N:26]=[CH:27][C:21]=4[NH:20][C:19]=3[N:18]=[CH:17][CH:16]=2)[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1)[CH3:2]
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 3

HCID 24758Sodium hydrideHCID 582666684-Chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrileHCID 58365113HCID 58365113、化合物

生成物 1

HCID 532507014-((4-ethyl-1-methylpiperidin-4-yl)methoxy)-9H-diprido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 8028
Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

To a solution of (4-ethyl-1-methylpiperidin-4-yl)methanol (223 mg, 1.4 mmol) in tetrahydrofuran (3.2 mL) was added sodium hydride as 60% dispersion in mineral oil (57 mg, 1.4 mmol). The reaction mixture was stirred at ambient temperature for 5 minutes before 4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (150 mg, 0.42 mmol) was added in one portion and the reaction mixture was stirred at this temperature for 10 minutes, and then heated at 40° C. for 4 hours. The mixture was diluted with water (20 mL) and ethyl acetate (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 0-10% methanol in methylene chloride) to afford the title compound as a white foam, which was used in the next step without any further purification (152 mg, 76%).

後処理

  1. additionwas added in one portion
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified flash chromatography (silica, 4 g, ISCO, 0-10% methanol in methylene chloride)

出典と根拠

ORDレコード
ord-8d9a85c2eefe40389a7517f27383710a
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09440976B2

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