Tetrahydrofuran → 4-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)-benzoic acid ethyl ester

HRID 51700

반응식

HRID 51700 반응식
COC(=O)C1C=CC(C#C[C:12]2[CH:13]=[C:14]([CH:26]3[CH2:28]C3)[C:15]3O[C:19]4(CC4)[CH2:18][C:17]([CH3:24])([CH3:23])[C:16]=3[CH:25]=2)=CC=1F.[C:31](O)(=O)[C:32]1[CH:37]=CC=CC=1.[CH2:40]([O:42][C:43](=[O:51])[C:44]1[CH:49]=[CH:48][C:47](I)=[CH:46][CH:45]=1)[CH3:41].C([N:54](CC)CC)C.O1CCCC1>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.C(OCC)(=O)C>[CH2:40]([O:42][C:43](=[O:51])[C:44]1[CH:49]=[CH:48][C:47]([C:28]#[C:26][C:14]2[CH:15]=[C:16]3[C:25](=[CH:12][CH:13]=2)[N:54]([CH:32]2[CH2:31][CH2:37]2)[CH2:19][CH2:18][C:17]3([CH3:23])[CH3:24])=[CH:46][CH:45]=1)[CH3:41]

참가 물질

9

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 695484184-[(8-Cyclopropyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester2회HCID 69887287Ethyl-4-iodo-benzoate benzoate2회

생성물 1

HCID 695488784-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)-benzoic acid ethyl ester

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

Following general procedure F and using 1-cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydro quinoline (Intermediate 53, 0.11 g, 0.43 mmol), ethyl-4-iodo-benzoate (Reagent A, 0.11 g, 0.9 mmol), triethyl amine (3 mL), tetrahydrofuran(3 mL), copper(I)iodide(0.02 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.060 g, 0.085 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.05 g, 31%).

출처 및 근거

ORD 기록
ord-f2bbddee128a4ed2b72a7fa8e8009d16
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713647B2

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