Tetrahydrofuran → [4-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)phenyl]acetic Acid Methyl Ester

HRID 841383Notes

Reaction equation

HRID 841383 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.[CH3:31][O:32][C:33](=[O:42])[CH2:34][C:35]1[CH:40]=[CH:39][C:38](I)=[CH:37][CH:36]=1.C([N:45]([CH2:48][CH3:49])CC)C.O1CCC[CH2:51]1>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>[CH3:31][O:32][C:33](=[O:42])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:28]#[C:26][C:14]2[CH:15]=[C:16]3[C:25](=[CH:12][CH:13]=2)[N:45]([CH:48]2[CH2:49][CH2:51]2)[CH2:19][CH2:18][C:17]3([CH3:23])[CH3:24])=[CH:37][CH:36]=1

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10378700Methyl 4-Iodophenylacetate2×HCID 695484184-[(8-Cyclopropyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester2×

Product 1

HCID 10270709[4-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)phenyl]acetic Acid Methyl 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, 0.05 g, 0.22 mmol), methyl-4-iodo-phenyl acetate (Reagent B, 0.055 g, 0.2 mmol), triethyl amine (5 mL), tetrahydrofuran, copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.75 g, 0.11 mmol) followed preparative normal phase HPLC using 10% ethyl acetate in hexane as the mobile phase, the title compound was obtained (0.089 g, 100%).

Sources & evidence

ORD record
ord-311e01b86f3042afb9fb2c46c0a42c4c
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

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