Triethylamine → 2-{4-[5-(Cyclopropyl-methyl-amino)-4-methoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-propionic acid methyl ester

HRID 1765788Notes

Reaction equation

HRID 1765788 reaction equation
[CH:1]1([N:4]([CH3:21])[CH:5]2[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]3C(OC)=C(C#C)C=C[C:6]2=3)[CH2:3][CH2:2]1.[CH3:22][O:23][C:24](=[O:52])[CH:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33]#[C:34][C:35]2[CH:36]=C(C3CC3)C3OC4(CC4)CC(C)(C)[C:39]=3[CH:48]=2)=[CH:29][CH:28]=1)[CH3:26].C(N(CC)CC)C.[C:60](OCC)(=[O:62])C>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>[CH3:22][O:23][C:24](=[O:52])[CH:25]([C:27]1[CH:28]=[CH:29][C:30]([C:33]#[C:34][C:35]2[CH:48]=[C:39]([O:62][CH3:60])[C:6]3[CH:5]([N:4]([CH:1]4[CH2:3][CH2:2]4)[CH3:21])[CH2:14][CH2:13][C:12]([CH3:15])([CH3:16])[C:11]=3[CH:36]=2)=[CH:31][CH:32]=1)[CH3:26]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 211071965-(Cyclopropyl-methyl-amino)-2-ethynyl-8,8-dimethyl-methoxy-5,6,7,8-tetrahydro-naphthalene2×HCID 690752312-{4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-phenyl}-propionic acid methyl ester2×

Product 1

HCID 574242452-{4-[5-(Cyclopropyl-methyl-amino)-4-methoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-propionic acid methyl ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent

Procedure

Following General Procedure B and using 5-(cyclopropyl-methyl-amino)-2-ethynyl-8,8-dimethyl-4-methoxy-5,6,7,8-tetrahydro-naphthalene (Intermediate 81, 0.085 g, 0.30 mmol), methyl-2-(4-iodophenyl)propionate (Reagent 1, 0.087 g, 0.3 mmol), triethyl amine (8 mL), copper(I)iodide (0.019 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.07 g, 0.1 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 5–20% ethyl acetate in hexane as the eluent, the title compound was obtained as a yellow solid (0.115 g, 86%).

Sources & evidence

ORD record
ord-00f8a1ec6af54cc9ba245dba5be2bff4
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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