Triethylamine → HCID 69212794, compound

HRID 898671Notes

Reaction equation

HRID 898671 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([C:13]#[C:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=1)[O:9][C:8]([CH3:20])([CH3:19])[CH2:7][C:6]2([CH3:22])[CH3:21])#[CH:2].[CH3:23][O:24][C:25](=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30](I)=[CH:29][C:28]=1[F:34].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>[CH3:23][O:24][C:25](=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:10](=[C:11]([C:13]#[C:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=2)[O:9][C:8]([CH3:20])([CH3:19])[CH2:7][C:6]3([CH3:22])[CH3:21])=[CH:29][C:28]=1[F:34]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 187102252-Fluoro-4-iodo phenyl acetic acid methyl esterHCID 600838886-Ethynyl-8-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman

Product 1

HCID 69212794HCID 69212794, 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 J and using 6-ethynyl-8-trimethylsilanylethylnyl-2,2,4,4-tetramethyl chroman (Compound 37, 0.1 g, 0.32 mmol), 2-fluoro-4-iodo phenyl acetic acid methyl ester (see U.S. Pat. No. 6,252,090, 0.095 g, 0.32 mmol), triethyl amine, copper(I)iodide (0.019 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.071 g, 0.1 mmol), followed by flash column chromatography over silica gel (230-400 mesh) using 4-10% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (0.11 g, 72%).

Sources & evidence

ORD record
ord-52dbb16ca4ca41dda155fbafe905575d
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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