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

HRID 51700

反応式

HRID 51700 の反応式
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]

参加物

9

反応物 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 ester2 回HCID 69887287Ethyl-4-iodo-benzoate benzoate2 回

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

出典と根拠

ORDレコード
ord-f2bbddee128a4ed2b72a7fa8e8009d16
出典データセット
uspto-grants-2004_03
特許番号
US06713647B2

関連ノート

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