Triethylamine → HCID 69076258, compound

HRID 1869968Notes

Reaction equation

HRID 1869968 reaction equation
[CH:1]([O:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][C:9]([C:12]#[CH:13])=[CH:8][C:7]=1[CH2:14][N:15]([CH:17]1[CH2:19][CH2:18]1)[CH3:16])([CH3:3])[CH3:2].[CH3:21][O:22][C:23](=[O:51])[CH:24]([C:26]1[CH:31]=[CH:30][C:29](C#CC2C=C(C3CC3)C3OC4(CC4)CC(C)(C)C=3C=2)=[CH:28][CH:27]=1)C.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>[CH:1]([O:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:29]2[CH:30]=[CH:31][C:26]([CH2:24][C:23]([O:22][CH3:21])=[O:51])=[CH:27][CH:28]=2)=[CH:8][C:7]=1[CH2:14][N:15]([CH:17]1[CH2:19][CH2:18]1)[CH3:16])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 57424255HCID 57424255, compound2×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 69076258HCID 69076258, 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 2-[(cyclopropyl-methyl-amino)methyl]-4-ethynyl-benzoic acid isopropyl ester (Intermediate 122, 0.07 g, 0.26 mmol), methyl-2-(4-iodophenyl)-propionate (Reagent 1, 0.081 g, 0.29 mmol), triethyl amine (2 mL), copper(I)iodide (0.03 g, 0.158 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.07 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 10-15% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (0.09 g, 81%).

Sources & evidence

ORD record
ord-3c2cbc6e7ff74f5aac72ebebeb417179
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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