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

HRID 1936134Notes

Reaction equation

HRID 1936134 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9]1([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][Si:27]([C:30]#[CH:31])([CH3:29])[CH3:28]>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]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9]1([C:12]2[CH:17]=[CH:16][C:15]([C:31]#[C:30][Si:27]([CH3:29])([CH3:28])[CH3:26])=[CH:14][CH:13]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 22568917Dibenzyl-[1-(4-bromophenyl)-cyclopropyl]-amine2×

Product 1

HCID 22568993Dibenzyl-[1-(4-trimethylsilanylethynylphenyl)-cyclopropyl]-amineYield 88%

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; dibenzyl-[1-(4-bromophenyl)-cyclopropyl]-amine (Intermediate 125, 45.0 mg, 0.1 1 mmol) in triethylamine (8 mL) was treated with copper(I)iodide (10.0 mg, 0.05 mmol) and then sparged with argon for 5 minutes. Trimethylsilyl acetylene (0.35 g, 3.6 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 40 mg (88%) was isolated by chromatography (hexanes).

Workup

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

Sources & evidence

ORD record
ord-2cf1be765bd04842a5f9be27b122e891
Source dataset
uspto-grants-2002_05
Patent number
US06387951B1

Reaction notes

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