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Piperidine → Ethyl 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-1h-indole-2-carboxylate

HRID 1916739
ノート
印刷プレビュー

反応式

HRID 1916739 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:6]2[CH3:24])#[CH:2].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:33]=[CH:34][C:35](I)=[N:36][CH:37]=2)=[CH:28][CH:27]=1.N1CCCCC1>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[CH:33]=[CH:34][C:35]([C:2]#[C:1][C:3]3[CH:4]=[C:5]4[C:9](=[CH:10][CH:11]=3)[N:8]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:6]4[CH3:24])=[N:36][CH:37]=2)=[CH:30][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 8082PiperidineHCID 859698495-(4-Chlorophenyl)-2-iodopyridineHCID 86594685ethyl 5-ethynyl-3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-1H-indole-2-carboxylate

生成物 1

HCID 59835807Ethyl 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-1h-indole-2-carboxylate

試薬・触媒・溶媒 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

Under an argon atmosphere 11 mg (0.02 mmol) Pd(PPh3)2Cl2 and 3 mg (0.02 mmol) CuI are added to a solution of 250 mg (0.77 mmol) ethyl 5-ethynyl-3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-1H-indole-2-carboxylate and 243 mg (0.77 mmol) 5-(4-chloro-phenyl)-2-iodo-pyridine in 1.52 mL (15.4 mmol) piperidine and 25 mL THF and the reaction mixture is stirred for 4 h at RT. It is diluted with water, extracted exhaustively with EtOAc, the combined organic phases are washed with water and saturated NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified first by chromatography (silica gel, cyc/EtOAc 2:1) and then by HPLC.

後処理

  1. extractionextracted exhaustively with EtOAc
  2. washthe combined organic phases are washed with water and saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customis purified first by chromatography (silica gel, cyc/EtOAc 2:1)

出典と根拠

ORDレコード
ord-1125257b5b994b22879578fb6a67031a
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08618132B2

反応ノート

読み込み中…

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