1-Ethynyl-4-propoxybenzene → HCID 66613508, compound

HRID 76201Notes

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

Participants

Conditions

Temperature: 80 °C

Procedure

To 0.33 g (1.00 mmol) trifluoromethanesulfonic acid 4-(2-acetylamino-propyl)-phenyl ester (I53.2) and 0.18 g (1.10 mmol) 1-ethynyl-4-propoxybenzene in 3 mL DMF and 0.60 mL (4.50 mmol) TEA are added 0.04 g (0.06 mmol) bis-(triphenylphosphin)-palladiumdichlorid. The mixture is stirred in a sealed tube at 80° C. for 24 h. The reaction mixture is partitioned between EtOAc and water, the organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatographie (silica gel, DCM/EtOAc 1/1). The resulting product is triturated with diethylether and dried at 80° C. in vacuo.

Workup

customThe reaction mixture is partitioned between EtOAc and water
dry with materialthe organic layer is dried with Na2SO4
customthe solvent is removed in vacuo
customThe residue is purified by column chromatographie (silica gel, DCM/EtOAc 1/1)
customThe resulting product is triturated with diethylether
customdried at 80° C. in vacuo

Sources & evidence

ORD record: ord-07cc6972bbba45a1a6b1aa91f33e7fcd
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835472B2

Reaction notes

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