2-Hydroxy-4-iodobenzoic acid → 4-[3-(3-Tert-butyl-5-chloro-4-dimethylaminophenyl)-3-hydroxyprop-1-ynyl]-2-hydroxybenzoic acid

HRID 1698416Notes

Reaction equation

HRID 1698416 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].[C:12]([C:16]1[CH:17]=[C:18]([CH:26]([OH:29])[C:27]#[CH:28])[CH:19]=[C:20]([Cl:25])[C:21]=1[N:22]([CH3:24])[CH3:23])([CH3:15])([CH3:14])[CH3:13]>[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>[C:12]([C:16]1[CH:17]=[C:18]([CH:26]([OH:29])[C:27]#[C:28][C:9]2[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([OH:1])[CH:10]=2)[CH:19]=[C:20]([Cl:25])[C:21]=1[N:22]([CH3:23])[CH3:24])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 728742-Hydroxy-4-iodobenzoic acidHCID 866465721-(3-Tert-butyl-5-chloro-4-dimethylaminophenyl)prop-2-yn-1-ol

Product 1

HCID 251095614-[3-(3-Tert-butyl-5-chloro-4-dimethylaminophenyl)-3-hydroxyprop-1-ynyl]-2-hydroxybenzoic acidYield 42%

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 220 mg (0.83 mmol) of 2-hydroxy-4-iodobenzoic acid with 320 mg (1.2 mmol) of 1-(3-tert-butyl-5-chloro-4-dimethylaminophenyl)prop-2-yn-1-ol in the presence of 9 mg (0.05 mmol) of copper iodide and 17 mg (0.025 mmol) of bis(triphenyl-phosphine)palladium chloride. 140 mg of 4-[3-(3-tert-butyl-5-chloro-4-dimethylaminophenyl)-3-hydroxyprop-1-ynyl]-2-hydroxybenzoic acid are obtained in the form of a yellowish oil (Mp=175° C., yield=42%).

Sources & evidence

ORD record
ord-aecb94d8328d4527821f2ce42815ae1f
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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