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

HRID 1765802
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HRID 1765802 반응식
[CH:1]1([N:4]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[CH:14])[CH:8]=2)[CH3:5])[CH2:3][CH2:2]1.Br[C:16]1[CH:17]=[C:18]2[C:23](=[C:24](CNC3CC3)[CH:25]=1)[O:22][C:21](C)(C)[CH2:20][C:19]2(C)C.[CH2:35](N(CC)CC)C.[C:42](OCC)(=[O:44])[CH3:43]>CCCCCC.[Cu]I>[CH2:42]([O:44][C:21](=[O:22])[C:20]([CH3:35])=[CH:19][C:18]1[CH:17]=[CH:16][C:25]([C:14]#[C:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][N:4]([CH:1]3[CH2:3][CH2:2]3)[CH3:5])[CH:8]=2)=[CH:24][CH:23]=1)[CH3:43]
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 211072186-Bromo-8-[(cyclopropyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman2회HCID 21107260Cyclopropyl-(3-ethynyl-benzyl)-methyl-amine2회

생성물 1

HCID 690699743-(4-{3-[(Cyclopropyl-methyl-amino)-methyl]-phenylethynyl}-phenyl)-2-methyl-acrylic acid ethyl ester

시약·촉매·용매 2

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

실험 절차

Following General Procedure B and using cyclopropyl-(3-ethynyl-benzyl)-methyl-amine (Intermediate 91, 0.1 g, 0.54 mmol), (E)-3-(4-iodo-phenyl)-2-methyl-acrylic acid ethyl ester (Reagent 7, 0.17 g, 0.54 mmol), triethyl amine (10 mL), copper(I)iodide (0.019 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II)—(0.71 g, 0.1 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 2–10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.15 g, 75%). 1H NMR (300 MHz, CDCl3): δ 7.66–7.25 (m, 9H), 4.27 (q, J=7.3 Hz, 2H), 3.65 (s, 2H), 2.25 (s, 3H), 2.13 (d, J=1.2 Hz, 3H), 1.75–1.65 (m, 1H), 1.35 (t, J=7.3 Hz, 3H), 0.50–0.40 (m, 4H).

출처 및 근거

ORD 기록
ord-cbae67c7c8ed4291a65286210237f7ae
출처 데이터셋
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07226951B2

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