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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
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HRID 1916739 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 962Water용매
HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1125257b5b994b22879578fb6a67031a
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08618132B2

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