4-(3-Butyn-1-yl)benzenemethanol → (4-{4-[5-(4-Chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-phenyl)-methanol

HRID 1916534

반응식

HRID 1916534 반응식
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1)[CH2:2][C:3]#[CH:4].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23](I)=[N:24][CH:25]=2)=[CH:16][CH:15]=1>C(N(CC)CC)C.CN(C=O)C.CCOC(C)=O.CO.[Cu]I.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>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]=[CH:22][C:23]([C:4]#[C:3][CH2:2][CH2:1][C:5]3[CH:6]=[CH:7][C:8]([CH2:11][OH:12])=[CH:9][CH:10]=3)=[N:24][CH:25]=2)=[CH:18][CH:19]=1

참가 물질

9

반응물 2

HCID 235966094-(3-Butyn-1-yl)benzenemethanolHCID 859698495-(4-Chlorophenyl)-2-iodopyridine

생성물 1

HCID 69071295(4-{4-[5-(4-Chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-phenyl)-methanol

시약·촉매·용매 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

반응 조건

온도
65 °C

실험 절차

Under a nitrogen atmosphere 76 mg (0.4 mmol) CuI and 281 mg (0.4 mmol) Pd(PPh3)2Cl2 are added to a solution of 1.27 g (7.92 mmol) (4-but-3-ynyl-phenyl)-methanol and 2.5 g (7.92 mmol) 5-(4-chloro-phenyl)-2-iodo-pyridine in 40 mL triethylamine and 20 mL DMF and the reaction mixture is stirred for 2 h at 65° C. The solvent is eliminated in vacuo, the residue is dissolved in a little EtOAc and MeOH and purified by chromatography on silica gel (gradient: cyc/EtOAc 3:1 to cyc/EtOAc 1:1).

후처리

  1. custompurified by chromatography on silica gel (gradient: cyc/EtOAc 3:1 to cyc/EtOAc 1:1)

출처 및 근거

ORD 기록
ord-b017d4da26884d0cb229c05bd861d94d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

연결된 노트

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