Triethylamine → (E)-3-(4-{5-[(Cyclopropyl-methyl-amino)-methyl]-2-methyl-phenylethynyl}-phenyl)-acrylic acid ethyl ester

HRID 1765809노트

반응식

HRID 1765809 반응식
[CH:1]1([N:4]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([C:14]#[CH:15])[CH:8]=2)[CH3:5])[CH2:3][CH2:2]1.[CH2:16]([O:18][C:19](=[O:48])/[C:20](/C)=[CH:21]/[C:22]1[CH:27]=[CH:26][C:25](C#CC2C=C(C3CC3)C3OC4(CC4)C(C)=C(C)C=3C=2)=[CH:24][CH:23]=1)[CH3:17].C(N(CC)CC)C.C(OCC)(=O)C>CCCCCC.[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>[CH2:16]([O:18][C:19](=[O:48])/[CH:20]=[CH:21]/[C:22]1[CH:27]=[CH:26][C:25]([C:15]#[C:14][C:9]2[CH:8]=[C:7]([CH2:6][N:4]([CH:1]3[CH2:3][CH2:2]3)[CH3:5])[CH:12]=[CH:11][C:10]=2[CH3:13])=[CH:24][CH:23]=1)[CH3:17]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21107259Cyclopropyl-(3-ethynyl-4-methylbenzyl)-methyl-amine2회HCID 69069630(E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid ethyl ester2회

생성물 1

HCID 57462494(E)-3-(4-{5-[(Cyclopropyl-methyl-amino)-methyl]-2-methyl-phenylethynyl}-phenyl)-acrylic acid ethyl ester

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8058Hexane용매

실험 절차

Following General Procedure B and using cyclopropyl-(3-ethynyl-4-methyl-benzyl)-methyl-amine (Intermediate 99, 0.095 g, 0.48 mmol), ethyl-4-iodo-cinnamate (Reagent 3, 0.144 g, 0.47 mmol), triethyl amine (13 mL), copper(I)iodide (0.019 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.071 g, 0.1 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 5–20% ethyl acetate in hexane as the eluent, the title compound was obtained (0.14 g, 82%).

출처 및 근거

ORD 기록
ord-5ffef9e312244cf3ab90130ce28f0301
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07226951B2

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