4-tert-Butylphenylacetylene → N-{2-[4-(4-tert-Butylphenylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

HRID 76202Notes

Reaction equation

[C:1]([NH:4][CH:5]([CH3:21])[CH2:6][C:7]1[CH:12]=[CH:11][C:10](OS(C(F)(F)F)(=O)=O)=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[C:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32]#[CH:33])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>O.C(N)(CC)C.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:22]([C:26]1[CH:27]=[CH:28][C:29]([C:32]#[C:33][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH3:21])=[CH:8][CH:9]=2)=[CH:30][CH:31]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To 0.50 g (1.54 mmol) trifluoro-methanesulfonic acid 4-(2-acetylamino-propyl)-phenyl ester (I53.2) and 0.32 g (2.00 mmol) 4-tert.butylphenylacetylen in 3.0 mL water and 3.0 mL sec-butylamine are added 0.10 g (0.14 mmol) bis(triphenyphosphine)dichloropalladium and the mixture is stirred at r.t. for 4 h and at 80° C. for 1 h. The reaction mixture is allowed to cool to r.t. and is then partitioned between EtOAc and citric acid (10% in water). The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified twice by column chromatography (silica gel; DCM/MeOH 9/1 and aluminium oxide DCM/EtOAc 4/1). The resulting product is triturated with MeOH.

Workup

temperatureto cool to r.t.
customis then partitioned between EtOAc and citric acid (10% in water)
dry with materialThe organic layer is dried with Na2SO4
customthe solvent is removed in vacuo
customThe residue is purified twice by column chromatography (silica gel; DCM/MeOH 9/1 and aluminium oxide DCM/EtOAc 4/1)
customThe resulting product is triturated with MeOH

Sources & evidence

ORD record: ord-e58ca687cc9f42409872511eb34a28f0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835472B2

Reaction notes

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