Trimethylsilylacetylene → Benzyl-[-(4-trimethylsilanylethynyl-phenyl)-cyclopropyl]-methylamine

HRID 841714Notes

Reaction equation

HRID 841714 reaction equation
[CH2:1]([N:8]([C:10]1([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22]>C(N(CC)CC)C.[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>[CH2:1]([N:8]([C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:25]#[C:24][Si:21]([CH3:23])([CH3:22])[CH3:20])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 22568936Benzyl-[1-(4-bromophenyl)-cyclopropyl]-methylamine2×

Product 1

HCID 69548036Benzyl-[-(4-trimethylsilanylethynyl-phenyl)-cyclopropyl]-methylamineYield 85.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

Using General Procedure D; benzyl-[1-(4-bromophenyl)-cyclopropyl]-methylamine (Intermediate 130, 90.0 mg, 0.28 mmol) in triethylamine (8 mL) was treated with copper(I)iodide (6.0 mg, 0.03 mmol) and then sparged with argon for 5 minutes. Trimethylsilyl acetylene (0.70 g, 7.1 mmols) was then added followed by dichlorobis(triphenylphosphine)palladium(II) (20.0 mg, 0.03 mmol). The resulting reaction mixture was heated to 70° C. for 5 days. The title compound 80 mg (84%) was isolated by chromatography (0-2% EtOAc-hexanes).

Workup

  1. customsparged with argon for 5 minutes
  2. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-606f03c6bb2f40608deb6ec48a3cd585
Source dataset
uspto-grants-2002_04
Patent number
US06369261B1

Reaction notes

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