(Triethylsilyl)acetylene → 2-(2-((Triethylsilyl)ethynyl)phenyl)propanamide

HRID 592354Notes

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].[C:13]([Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])#[CH:14].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>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.[Cu]I>[CH2:16]([Si:15]([C:13]#[C:14][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([NH2:11])=[O:10])([CH2:20][CH3:21])[CH2:18][CH3:19])[CH3:17]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-(2-iodophenyl)propanamide I13 (12.4 g, 45.2 mmol), ethynyltriethylsilane (9.72 mL, 54.2 mmol), PdCl2(PPh3)2 (0.634 g, 0.904 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.262 g, 0.904 mmol) and CuI (0.172 g, 0.904 mmol) in DMF (46 mL) was stirred under a nitrogen atmosphere at 70° C. for 4 hours. The volatiles were removed in vacuo and the crude residue was purified by silica gel column chromatography (Combiflash Rf, 0-30% EtOAc in cyclohexane) to give the title compound I14 as an orange oil (8.9 g, 68%). LCMS-B: rt 3.845 min; m/z 288 [M+H]+.

Workup

customThe volatiles were removed in vacuo
customthe crude residue was purified by silica gel column chromatography (Combiflash Rf, 0-30% EtOAc in cyclohexane)

Sources & evidence

ORD record: ord-fbf5c6d2131b43f1b3590cb39128545d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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