Trimethylsilylacetylene → HCID 57809256, compound

HRID 2105854Notes

Reaction equation

[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[C:7](I)=[CH:8][C:9]([O:17][CH2:18][CH3:19])=[C:10]([CH:16]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:5])=[O:4].[CH3:22][Si:23]([C:26]#[CH:27])([CH3:25])[CH3:24]>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)I.C(N(CC)CC)C>[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[C:7]([C:27]#[C:26][Si:23]([CH3:25])([CH3:24])[CH3:22])=[CH:8][C:9]([O:17][CH2:18][CH3:19])=[C:10]([CH:16]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:5])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl 5-dimethylsulfamoyl-2-ethoxy-4-iodobenzoate (0.142 g, 0.332 mmol; prepared as described in example 14), dichlorobis(triphenylphosphine)palladium(II) (0.023 g, 0.032 mmol), copper(II) iodide (3.2 mg, 0.017 mmol) dimethylformamide (0.5 mL), triethylamine (0.5 mL) and (trimethylsilyl)acetylene (0.066 mL, 0.47 mmol) were added sequentially to a flame-dried Schienk tube. The reaction mixture was heated at 50° C. oil bath for 2 h, allowed to cool to room temperature overnight and then partitioned between water (20 mL) and diethyl ether (3×20 mL), dried over magnesium sulfate and evaporated. The residue was purified by flash column chromatography (eluting with 20% ethyl acetate in hexanes) to give ethyl 5-dimethylsulfamoyl-2-ethoxy-4-trimethylsilanylethynylbenzoate as an off-white glass (0.111 g, 84%). LC-MS: 398.3 [(M+H)+].

Workup

temperatureto cool to room temperature overnight
custompartitioned between water (20 mL) and diethyl ether (3×20 mL)
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was purified by flash column chromatography (eluting with 20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-19ada08ab71e442191ed7bc89b73f549
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579368B2

Reaction notes

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