Dimethylformamide → N-(1-(4-((4-hydroxyphenyl)ethynyl)phenyl)propan-2-yl)acetamide

HRID 76180Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=1)#[CH:2].I[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.CN(C=O)C.[NH4+].[Cl-]>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4.00 g (19.9 mmol) of N-(1-(4-ethynylphenyl)propan-2-yl)acetamide (I58.3) and 5.25 g (23.9 mmol) 4-iodophenol are added to 125 ml of a 1:1 mixture of DMF and TEA. After cooling down to 0° C. 189 mg (0.99 mmol) CuI and 976 mg (1.39 mmol) Pd(PPh3)4 are added. After stirring over night at r.t. the mixture is treated with EtOAc and sat. NH4Cl solution. The organic layer is washed with brine, dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, EtOAc).

Workup

washThe organic layer is washed with brine
dry with materialdried with Na2SO4
customthe solvent is removed in vacuo
customThe residue is purified by column chromatography (silica gel, EtOAc)

Sources & evidence

ORD record: ord-f207fb7ac1ed462ca1e41ac0883593ec
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835472B2

Reaction notes

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