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

HRID 51700

Reaction equation

HRID 51700 reaction equation
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]

Participants

9

Reactant 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×HCID 69887287Ethyl-4-iodo-benzoate benzoate2×

Product 1

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

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Sources & evidence

ORD record
ord-f2bbddee128a4ed2b72a7fa8e8009d16
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Linked notes

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