4-Iodobenzoic acid → 4-[3-(4-Diethylamino-3-isopropylphenyl)-3-hydroxyprop-1-ynyl]benzoic acid

HRID 1698423Notes

Reaction equation

HRID 1698423 reaction equation
I[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH2:11]([N:13]([CH2:27][CH3:28])[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([OH:23])[C:21]#[CH:22])=[CH:16][C:15]=1[CH:24]([CH3:26])[CH3:25])[CH3:12]>[Cu](I)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>[CH2:27]([N:13]([CH2:11][CH3:12])[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([OH:23])[C:21]#[C:22][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)=[CH:16][C:15]=1[CH:24]([CH3:26])[CH3:25])[CH3:28]

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 866465761-(4-Diethylamino-3-isopropylphenyl)prop-2-yn-1-ol

Product 1

HCID 672766054-[3-(4-Diethylamino-3-isopropylphenyl)-3-hydroxyprop-1-ynyl]benzoic acidYield 65.7%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

In a manner analogous to example 1 f, the process is carried out by a reaction of 248 mg (1 mmol) of 4-iodobenzoic acid with 350 mg (1.4 mmol) of 1-(4-diethylamino-3-isopropylphenyl)prop-2-yn-1-ol in the presence of 11 mg (0.06 mmol) of copper iodide and 20 mg (0.03 mmol) of bis(triphenylphosphine)palladium chloride. 240 mg of 4-[3-(4-diethylamino-3-isopropylphenyl)-3-hydroxyprop-1-ynyl]benzoic acid are obtained in the form of a whitish solid (Mp=145° C., yield=46%).

Sources & evidence

ORD record
ord-cb25971327b1424a89abf89edc22f315
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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