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

HRID 2299469Notes

Reaction equation

HRID 2299469 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>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]([N:11]([CH2:15][CH2:16][CH3:17])[C:8]1([C:5]2[CH:6]=[CH:7][C:2]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[CH:3][CH:4]=2)[CH2:10][CH2:9]1)[CH2:13][CH3:14]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 22568796[1-(4-Bromophenyl)-cyclopropyl]dipropylamine2×

Product 1

HCID 22568945Dipropyl-[1-(4-trimethylsilanylethynylphenyl)-cyclopropyl]-amine

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]-dipropylamine (Intermediate 121, 150.0 mg, 0.50 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (10.0 mg, 0.05 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) (35.0 mg, 0.05 mmol). The resulting reaction mixture was heated to 70° C. for 5 d. The title compound was isolated by chromatography (0-3% EtOAc-hexanes).

Workup

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

Sources & evidence

ORD record
ord-3d9a46dc27ce4417a70ebe3564c528db
Source dataset
uspto-grants-2002_12
Patent number
US06495552B2

Reaction notes

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