Triethylamine → HCID 58883450, compound

HRID 2377528Notes

Reaction equation

HRID 2377528 reaction equation
[CH:1]([O:4][C:5](=[O:16])[C:6]1[CH:11]=[C:10]([C:12]#[CH:13])[CH:9]=[C:8]([C:14]#[CH:15])[CH:7]=1)([CH3:3])[CH3:2].[C:17]([O:20][CH2:21][O:22][C:23](=[O:33])[CH2:24][C:25]1[CH:30]=[CH:29][C:28](I)=[CH:27][C:26]=1[F:32])(=[O:19])[CH3:18].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:16])[C:6]1[CH:11]=[C:10]([C:12]#[CH:13])[CH:9]=[C:8]([C:14]#[C:15][C:28]2[CH:29]=[CH:30][C:25]([CH2:24][C:23]([O:22][CH2:21][O:20][C:17](=[O:19])[CH3:18])=[O:33])=[C:26]([F:32])[CH:27]=2)[CH:7]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 57424208HCID 57424208, compoundHCID 57424273HCID 57424273, compound2×

Product 1

HCID 58883450HCID 58883450, 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 3,5-diethynyl-benzoic acid isopropyl ester (Intermediate 206, 0.27 g, 1.27 mmol), (2-fluoro-4-iodo-phenyl)-acetic acid acetoxymethyl ester (0.224 g, 0.64 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 2.5-20% ethyl acetate in hexane as the eluent, the title compound was obtained as an orange solid (0.09 g, 32%).

Sources & evidence

ORD record
ord-e09b5d02ea7f401780db4fe49465f749
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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