4-Iodobenzoic acid → HCID 67276142, compound

HRID 1698399Notes

Reaction equation

HRID 1698399 reaction equation
[C:1]([C:5]1[CH:6]=[C:7](C(O)C#C)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:16][CH3:17])[CH2:12][CH:13]([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].I[C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=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[C:10]([N:11]([CH2:16][CH3:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[C:9]([CH:27]([OH:28])[C:26]#[C:25][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=2)[CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 120854-Iodobenzoic acidHCID 86646564HCID 86646564, compound

Product 1

HCID 67276142HCID 67276142, compoundYield 107.2%

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 300 mg (1 mmol) of 1-[3-tert-butyl-4-(ethylisobutylamino)phenyl]prop-2-yn-1-ol with 216 mg (0.87 mmol) of 4-iodobenzoic acid, 12 mg (0.04 mmol) of copper iodide and 15 mg (0.02 mmol) of bis(triphenylphosphine)palladium chloride. 190 mg of 4-{[tert-butyl(ethylisobutylamino)phenyl]hydroxyprop-1-ynyl}benzoic acid are obtained in the form of a beige solid (Mp=117° C., yield=53%).

Sources & evidence

ORD record
ord-990735edba69452fa0ad8f69f370e56b
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

Loading…