Triethylamine → HCID 69069738, compound

HRID 1870020Notes

Reaction equation

HRID 1870020 reaction equation
[CH:1]1([N:4]([CH:6]2[C:15]3[C:10](=[CH:11][C:12]([C:17]#[CH:18])=[C:13]([CH3:16])[CH:14]=3)[C:9]([CH3:20])([CH3:19])[CH2:8][CH2:7]2)[CH3:5])[CH2:3][CH2:2]1.[CH3:21][O:22][C:23](=[O:52])[C:24]([C:27]1[CH:32]=[CH:31][C:30](C#CC2C=C(C3CC3)C3OC4(CC4)CC(C)(C)C=3C=2)=[CH:29][CH:28]=1)([CH3:26])[CH3:25].C(N(CC)CC)C.C(OCC)(=O)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>[CH3:21][O:22][C:23](=[O:52])[C:24]([C:27]1[CH:28]=[CH:29][C:30]([C:18]#[C:17][C:12]2[C:13]([CH3:16])=[CH:14][C:15]3[CH:6]([N:4]([CH:1]4[CH2:3][CH2:2]4)[CH3:5])[CH2:7][CH2:8][C:9]([CH3:20])([CH3:19])[C:10]=3[CH:11]=2)=[CH:31][CH:32]=1)([CH3:26])[CH3:25]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21107265HCID 21107265, compound2×HCID 690773412-{4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-phenyl}-2-methyl-propionic acid methyl ester2×

Product 1

HCID 69069738HCID 69069738, compound

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 cyclopropyl-(6-ethynyl-4,4,7-trimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-methyl-amine (Intermediate 174, 0.1 g, 0.29 mmol), methyl-2-(4-iodophenyl)-2-methyl-propionate (Reagent 2, 0.09 g, 0.29 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 1-2% ethyl acetate in hexane as the eluent, the title compound was obtained (0.035 g, 26%).

Sources & evidence

ORD record
ord-6c5082d2e8fb4fa785e7e487f87c2b89
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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