Trimethylsilylacetylene → Propyl-[1-(4-trimethylsilanylethynylphenyl)-cyclopropyl]-amine

HRID 1861452Notes

Reaction equation

HRID 1861452 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:11][CH2:12][CH2:13][CH3:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17]>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>[CH2:12]([NH:11][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])=[CH:3][CH:4]=2)[CH2:10][CH2:9]1)[CH2:13][CH3:14]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 22568814[1-(4-Bromophenyl)-cyclopropyl]-propylamine2×

Product 1

HCID 22568956Propyl-[1-(4-trimethylsilanylethynylphenyl)-cyclopropyl]-amineYield 75.6%

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; [1-(4-bromophenyl)-cyclopropyl]-propylamine (Intermediate 118, 100.0 mg, 0.39 mmol) in triethylamine (8 mL) was treated with copper(I)iodide (13.0 mg, 0.06 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) (48.0 mg, 0.06 mmol). The resulting reaction mixture was heated to 70° C. for 5 days. The title compound (80.0 mg, 75%) was isolated by chromatography (0-10% EtOAc-hexanes) as an orange oil.

Workup

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

Sources & evidence

ORD record
ord-b1cb1586b8e44f8493114700676813a8
Source dataset
uspto-grants-2003_03
Patent number
US06531599B2

Reaction notes

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