4-Iodobenzoic acid → HCID 25109558, compound

HRID 1698406Notes

Reaction equation

HRID 1698406 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]([OH:19])[C:17]#[CH:18])[CH:8]=[CH:9][C:10]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].I[C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=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:16]([OH:19])[C:17]#[C:18][C:21]2[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)[CH:8]=[CH:9][C:10]=1[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 86646568HCID 86646568, compound

Product 1

HCID 25109558HCID 25109558, compoundYield 45.4%

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 640 mg (2.5 mmol) of 1-(3-tert-butyl-4-pyrrolidin-1-ylphenyl)prop-2-yn-1-ol with 520 mg (2.1 mmol) of 4-iodobenzoic acid, 20 mg (0.1 mmol) of copper iodide and 37 mg (0.05 mmol) of bis(triphenylphosphine)palladium chloride. 360 mg of 4-[3-(3-tert-butyl-4-pyrrolidin-1-ylphenyl)-3-hydroxyprop-1-ynyl]benzoic acid are obtained in the form of a beige solid (Mp=150° C., yield=46%).

Sources & evidence

ORD record
ord-3150ec703db5428fab8343adfdaceab3
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

Loading…