Triethylamine → Cyclopropyl-methyl-(3-trimethylsilanylethynyl-benzyl)-amine

HRID 1869930Notes

Reaction equation

HRID 1869930 reaction equation
[CH:1]1([N:4]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9](I)[CH:8]=2)[CH3:5])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>CCCCCC.[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>[CH:1]1([N:4]([CH3:5])[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:26]#[C:25][Si:22]([CH3:24])([CH3:23])[CH3:21])[CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 21107263Cyclopropyl-(3-iodo-benzyl)-methyl-amine2×

Product 1

HCID 57424247Cyclopropyl-methyl-(3-trimethylsilanylethynyl-benzyl)-amineYield 80%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent2×

Procedure

Following General Procedure D and using cyclopropyl-(3-iodo-benzyl)-methyl-amine (Intermediate 89, 0.97 g, 3.4 mmol), triethyl amine (10 mL), copper(I)iodide (0.051 g, 0.27 mmol), trimethylsilyl acetylene (2 mL, 14 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.19 g, 0.27 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using hexane-5% ethyl acetate in hexane as the eluent, the title compound (0.695 g, 80%) was obtained.

Sources & evidence

ORD record
ord-534fb62beadd425fa67a27777bb6b864
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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