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

HRID 1765790Notes

Reaction equation

HRID 1765790 reaction equation
[CH:1]1([N:4]([CH3:21])[CH:5]2[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]3[C:10](OC)=[C:9]([C:19]#[CH:20])[CH:8]=[CH:7][C:6]2=3)[CH2:3][CH2:2]1.[CH3:22][O:23][C:24](=[O:35])[C:25]([C:28]1[CH:33]=[CH:32][C:31](I)=[CH:30][CH:29]=1)([CH3:27])[CH3:26].C(N(CC)CC)C.[C:43](OCC)(=[O:45])C>CCCCCC.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:35])[C:25]([C:28]1[CH:33]=[CH:32][C:31]([C:20]#[C:19][C:9]2[CH:8]=[C:7]([O:45][CH3:43])[C:6]3[CH:5]([N:4]([CH:1]4[CH2:2][CH2:3]4)[CH3:21])[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]=3[CH:10]=2)=[CH:30][CH:29]=1)([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 211071965-(Cyclopropyl-methyl-amino)-2-ethynyl-8,8-dimethyl-methoxy-5,6,7,8-tetrahydro-naphthalene2×HCID 21107277Methyl-2-(4-iodophenyl)-2-methyl-propionate

Product 1

HCID 574242462-{4-[5-(Cyclopropyl-methyl-amino)-4-methoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-2-methyl-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 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, 0.090 g, 0.32 mmol), methyl-2-(4-iodophenyl)-2-methyl-propionate (Reagent-2, 0.097 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 solid (0.09 g, 78%).

Sources & evidence

ORD record
ord-5749cc2ed2cb479cb02c833e7f63c17c
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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