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Piperidine → n-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-3-methyl-pyridin-2-yl}-2-pyrrolidin-1-yl-acetamide

HRID 1916744
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HRID 1916744 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH3:18])[C:6]([NH:9][C:10](=[O:17])[CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:7][CH:8]=1)#[CH:2].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][C:29](I)=[N:30][CH:31]=2)=[CH:22][CH:21]=1.N1CCCCC1>C1COCC1.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:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:2]#[C:1][C:3]3[CH:4]=[C:5]([CH3:18])[C:6]([NH:9][C:10](=[O:17])[CH2:11][N:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)=[N:7][CH:8]=3)=[N:30][CH:31]=2)=[CH:24][CH:25]=1
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참가 물질

7

반응물 3

HCID 8082PiperidineHCID 85969661N-(5-ethynyl-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamideHCID 859698495-(4-Chlorophenyl)-2-iodopyridine

생성물 1

HCID 59835753n-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-3-methyl-pyridin-2-yl}-2-pyrrolidin-1-yl-acetamide

시약·촉매·용매 3

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

실험 절차

Under an argon atmosphere 4 mg (0.01 mmol) Pd(PPh3)2Cl2 and 1 mg (0.01 mmol) CuI are added to a solution of 73 mg (0.3 mmol) N-(5-ethynyl-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide and 95 mg (0.3 mmol) 5-(4-chloro-phenyl)-2-iodo-pyridine in 59 μL (0.6 mmol) piperidine and 10 mL THF and the reaction mixture is stirred for 30 min at RT. It is evaporated down i.vac., the residue is taken up in EtOAc, the organic phase is 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, EtOAc/MeOH/NH3 95:5:0.5) and then by HPLC.

후처리

  1. customIt is evaporated down i.vac
  2. washthe organic phase is washed with water and saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customis purified first by chromatography (silica gel, EtOAc/MeOH/NH3 95:5:0.5)

출처 및 근거

ORD 기록
ord-882ca5315ec14cd580d2a040b081342f
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08618132B2

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