Triethylamine → HCID 69070551, compound

HRID 2377465Notes

Reaction equation

HRID 2377465 reaction equation
[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[CH:13])[CH:7]=1)([CH3:3])[CH3:2].[CH2:15]([O:17][C:18](=[O:28])[CH2:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][C:21]=1[F:27])[CH3:16].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:14])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[C:13][C:23]2[CH:24]=[CH:25][C:20]([CH2:19][C:18]([O:17][CH2:15][CH3:16])=[O:28])=[C:21]([F:27])[CH:22]=2)[CH:7]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 18740710Ethyl 2-fluoro-4-iodophenylacetateHCID 57424260HCID 57424260, compound2×

Product 1

HCID 69070551HCID 69070551, 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-ethynyl-benzoic acid isopropyl ester (Intermediate 137, 0.099 g, 0.53 mmol), 2-fluoro-4-iodo phenyl acetic acid ethyl ester (0.164 g, 0.53 mmol), triethyl amine (3 mL), copper(I)iodide (0.01 g, 0.05 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.035 g, 0.5 mmol) followed by flash column chromatography over silica gel (230-400 -mesh) using 7-10% ethyl acetate in hexane as the eluent, the title compound was obtained as a light orange oil (0.08 g, 92%).

Sources & evidence

ORD record
ord-e5bc7ab80943430da5ad626405a12d40
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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