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Sodium hydride → (3-methylpiperidin-3-yloxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60281
ノート
印刷プレビュー

反応式

HRID 60281 の反応式
[CH3:1][C:2]1([OH:8])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[H-].[Na+].Cl[C:12]1[C:20]2[C:19]3[CH:21]=[C:22]([C:25]#[N:26])[N:23]=[CH:24][C:18]=3[N:17]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:16]=2[N:15]=[CH:14][CH:13]=1>O1CCCC1.O.C(OCC)(=O)C>[CH3:1][C:2]1([O:8][C:14]2[CH:13]=[CH:12][C:20]3[C:19]4[CH:21]=[C:22]([C:25]#[N:26])[N:23]=[CH:24][C:18]=4[N:17]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[C:16]=3[N:15]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]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 3

HCID 24758Sodium hydrideHCID 224966263-Methylpiperidin-3-olHCID 582666684-Chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

生成物 1

HCID 86656042(3-methylpiperidin-3-yloxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[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 3-methylpiperidin-3-ol (99 mg, 0.86 mmol) in tetrahydrofuran (3.2 mL) was added sodium hydride as 60% dispersion in mineral oil (35 mg, 0.86 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 (141 mg, 0.39 mmol) was added in one portion and the reaction mixture was stirred at this temperature for 10 minutes before being warmed to 40° C. for 5 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, 40 g, ISCO, 1-20% methanol in methylene chloride) to afford the title compound as an orange solid, which was used in the next step without any further purification (52 mg, 30%).

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, 40 g, ISCO, 1-20% methanol in methylene chloride)

出典と根拠

ORDレコード
ord-4dc02e597b6949f4a4cbf2ddf561d658
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