Trimethylsilylacetylene → 2-(2-((Trimethylsilyl)ethynyl)phenyl)propanamide

HRID 592356Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([NH2:11])=[O:10].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33]>CN(C=O)C.[Cu]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>[CH3:31][Si:32]([C:35]#[C:36][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([NH2:11])=[O:10])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-(2-iodophenyl)propanamide I13 (16.5 g, 0.060 mol), CuI (0.229 g, 1.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.348 g, 1.20 mmol), PdCl2(PPh3)2 (0.421 g, 0.600 mmol) and trimethylsilylacetylene (10.3 mL, 0.072 mol) in DMF (60 mL) was bubbled with N2 for 10 minutes. Et3N (50 mL) was then added and the mixture was stirred under nitrogen at 60° C. for 5 hours. The reaction mixture was cooled and the volatiles were removed in vacuo. The dark brown residue was adsorbed onto silica and purified by column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 0-30% EtOAc in petroleum benzine 40-60° C.) to give the title compound I15 as an orange oil (11.5 g, 78%). LCMS-D: rt 3.49 min; m/z 246 [M+H]+.

Workup

customwas bubbled with N2 for 10 minutes
additionEt3N (50 mL) was then added
temperatureThe reaction mixture was cooled
customthe volatiles were removed in vacuo
custompurified by column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 0-30% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record: ord-d60519605f4f4474a60e4e6da7644cdf
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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