4-Iodobenzoic acid → HCID 25109629, compound

HRID 1698409Notes

Reaction equation

HRID 1698409 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:17]([OH:20])[C:18]#[CH:19])[CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].I[C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1>[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:1]([C:5]1[CH:6]=[C:7]([CH:17]([OH:20])[C:18]#[C:19][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)[CH:8]=[CH:9][C:10]=1[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 86646570HCID 86646570, compound

Product 1

HCID 25109629HCID 25109629, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

In a manner analogous to example 1 e, the process is carried out by a reaction of 1.18 g (4.4 mmol) of 1-(3-tert-butyl-4-piperidin-1-ylphenyl)prop-2-yn-1-ol with 890 mg (3.6 mmol) of 4-iodobenzoic acid, 35 mg (0.18 mmol) of copper iodide and 63 mg (0.09 mmol) of bis(triphenylphosphine)palladium chloride. 650 mg of 4-[3-(3-tert-butyl-4-piperidin-1-ylphenyl)-3-hydroxyprop-1-ynyl]benzoic acid are obtained in the form of a beige solid (Mp=112° C., yield=46%).

Sources & evidence

ORD record
ord-eae0a5b0d4ba433f8b1795eb8c2af7c2
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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