2-Hydroxy-4-iodobenzoic acid → 4-[3-(4-Dimethylamino-3,5-diisopropylphenyl)-3-hydroxyprop-1-ynyl]-2-hydroxy-benzoic acid

HRID 1698419Notes

Reaction equation

HRID 1698419 reaction equation
[OH:1][C:2]1[CH:10]=[C:9](I)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][N:13]([CH3:30])[C:14]1[C:19]([CH:20]([CH3:22])[CH3:21])=[CH:18][C:17]([CH:23]([OH:26])[C:24]#[CH:25])=[CH:16][C:15]=1[CH:27]([CH3:29])[CH3:28]>[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>[CH3:30][N:13]([CH3:12])[C:14]1[C:19]([CH:20]([CH3:21])[CH3:22])=[CH:18][C:17]([CH:23]([OH:26])[C:24]#[C:25][C:9]2[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([OH:1])[CH:10]=2)=[CH:16][C:15]=1[CH:27]([CH3:29])[CH3:28]

Participants

5

Reactant 2

HCID 728742-Hydroxy-4-iodobenzoic acidHCID 866465731-(4-Dimethylamino-3,5-diisopropylphenyl)prop-2-yn-1-ol

Product 1

HCID 251095594-[3-(4-Dimethylamino-3,5-diisopropylphenyl)-3-hydroxyprop-1-ynyl]-2-hydroxy-benzoic acidYield 22.5%

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 360 mg (1.35 mmol) of 2-hydroxy-4-iodobenzoic acid with 500 mg (1.9 mmol) of 1-(4-dimethylamino-3,5-diisopropylphenyl)prop-2-yn-1-ol in the presence of 15 mg (0.08 mmol) of copper iodide and 27 mg (0.04 mmol) of bis(triphenylphosphine)-palladium chloride. 120 mg of 4-[3-(4-dimethylamino-3,5-diisopropylphenyl)-3-hydroxyprop-1-ynyl]-2-hydroxy-benzoic acid are obtained in the form of a yellowish solid (Mp: dec>250° C., yield=22%).

Sources & evidence

ORD record
ord-a093c376043b4fe583f93ba06b045a13
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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