Tetrahydrofuran → Cyclopropyl-methyl-(4-methyl-3-trimethylsilanylethynyl-benzyl)-amine

HRID 1765807Notes

Reaction equation

HRID 1765807 reaction equation
[CH:1]1([N:4]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9](Br)[CH:8]=2)[CH3:5])[CH2:3][CH2:2]1.C(N(CC)CC)C.O1CCCC1.[CH3:27][Si:28]([C:31]#[CH:32])([CH3:30])[CH3:29]>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.C(OCC)(=O)C>[CH:1]1([N:4]([CH3:5])[CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([C:32]#[C:31][Si:28]([CH3:30])([CH3:29])[CH3:27])[CH:8]=2)[CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 21107149Benzenemethanamine, 3-bromo-N-cyclopropyl-N,4-dimethyl-2×

Product 1

HCID 57424248Cyclopropyl-methyl-(4-methyl-3-trimethylsilanylethynyl-benzyl)-amineYield 94.1%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure D and using cyclopropyl-(3-bromo-4-methyl-benzyl)-methyl-amine (Intermediate 97, 2.24 g, 8.81 mmol), triethyl amine (10 mL), tetrahydrofuran (5 mL), copper(I)iodide (0.4 g, 2.1 mmol), trimethylsilyl acetylene (5 mL, 35.4 mmol) and dichlorobis(triphenylphosphine)palladium(II) (1.45 g, 2.06 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 6–10% ethyl acetate in hexane as the eluent, the title compound (2.25 g, 94%) was obtained.

Sources & evidence

ORD record
ord-777d5f67cb6e48649a6b76f2686969e6
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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