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

HRID 1869940Notes

Reaction equation

HRID 1869940 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-methylbenzyl)-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-5396c41feea7422482aa8358482a56fe
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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