Triethylamine → HCID 58883450, compound

HRID 1765909Notes

Reaction equation

HRID 1765909 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 2.06, 0.27 g, 1–0.27 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-e5db7ff261564a61a8f2b8458de12d2f
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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