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

HRID 1916728
ノート
印刷プレビュー

反応式

HRID 1916728 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7f244b21bd784ce089b91846959549f6
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

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