Water → N-Ethyl-2-[4-(4-isopropyl-phenylethynyl)-phenyl]-propionamide

HRID 330845Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:11]([NH:13][C:14](=[O:25])[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=1)[CH3:16])[CH3:12].CC(N)CC.O>C1COCC1.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>[CH2:11]([NH:13][C:14](=[O:25])[CH:15]([C:17]1[CH:18]=[CH:19][C:20]([C:23]#[C:24][C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=2)=[CH:21][CH:22]=1)[CH3:16])[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

To 0.025 g (0.10 mmol) 4-iodoisopropylbenzene are added 20 g (0.10 mmol) N-ethyl-2-(4-ethynyl-phenyl)-propionamide (XVII.1) in 1 mL THF, followed by the addition of 0.5 mL 2-butylamine and 0.75 mL water. Subsequently 3 mg (0.05 mmol) bis-(triphenylphosphine)-palladium dichloride are added and the mixture is stirred at 80° C. for 5 h. After that time, the solvent is removed. The residue is taken up in DMF and the desired product was purified using RP-HPLC (water/MeOH+0.1% TFA).

Workup

customAfter that time, the solvent is removed
customthe desired product was purified

Sources & evidence

ORD record: ord-7d36f555302f450f9e1af040160b5b28
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877754B2

Reaction notes

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