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Cesium carbonate → 5-(4-Chloro-phenyl)-2-[3-(4-pyrrolidin-1-ylmethyl-phenyl)-prop-2-ynyloxy]-pyridine

HRID 1916728
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HRID 1916728 반응식
C([O-])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]#[CH:23])=[N:18][CH:19]=2)=[CH:10][CH:9]=1.I[C:25]1[CH:36]=[CH:35][C:28]([CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:27][CH:26]=1>C1COCC1.[Cu]I>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]#[C:23][C:25]3[CH:26]=[CH:27][C:28]([CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:35][CH:36]=3)=[N:18][CH:19]=2)=[CH:10][CH:9]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 185258671-(4-Iodobenzyl)pyrrolidineHCID 859696065-(4-Chloro-phenyl)-2-prop-2-ynyloxy-pyridine

생성물 1

HCID 598357275-(4-Chloro-phenyl)-2-[3-(4-pyrrolidin-1-ylmethyl-phenyl)-prop-2-ynyloxy]-pyridine

시약·촉매·용매 2

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

실험 절차

Under an N2 atmosphere 221 mg (0.68 mmol) Cs2CO3, 4 mg (0.02 mmol) CuI and 23 mg (0.02 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 110 mg (0.45 mmol) 5-(4-chloro-phenyl)-2-prop-2-ynyloxy-pyridine and 129 mg (0.45 mmol) 1-(4-iodo-benzyl)-pyrrolidine in 9 mL THF and the reaction mixture is stirred for 4.5 h at RT. The mixture is evaporated down i. vac., the residue is combined with 20 mL 3% NH3 solution and 40 mL EtOAc, the organic phase is separated off and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified first by HPLC and then by chromatography (silica gel, DCM/MeOH/NH3 19:1:0.1).

후처리

  1. customThe mixture is evaporated down i
  2. customthe organic phase is separated off
  3. dry with materialdried over Na2SO4
  4. customis purified first by HPLC

출처 및 근거

ORD 기록
ord-7f244b21bd784ce089b91846959549f6
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08618132B2

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