Trimethylsilylacetylene → Cyclopropyl-ethyl-(2-methyl-4-trimethylsilanylethynyl-benzyl)-amine

HRID 1861500Notes

Reaction equation

HRID 1861500 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]([CH:10]2[CH2:12][CH2:11]2)[CH2:8][CH3:9])=[C:4]([CH3:15])[CH:3]=1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>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>[CH:10]1([N:7]([CH2:8][CH3:9])[CH2:6][C:5]2[CH:13]=[CH:14][C:2]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:3][C:4]=2[CH3:15])[CH2:12][CH2:11]1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 22568961(4-Bromo-2-methyl-benzyl)-cyclopropyl-ethyl-amine2×

Product 1

HCID 22568965Cyclopropyl-ethyl-(2-methyl-4-trimethylsilanylethynyl-benzyl)-amineYield 98.6%

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; (4-bromo-2-methyl-benzyl)-cyclopropyl-ethyl-amine (Intermediate 159, 620.0 mg, 2.31 mmols) in triethylamine (8 mL) was treated with copper(I)iodide (44.0 mg, 0.23 mmol) and then sparged with argon for 15 minutes. Trimethylsilylacetylene (1.04 g, 10.6 mmols) was then added followed by dichlorobis-(triphenylphosphine)palladium(II) (162.0 mg, 0.23 mmol). The resulting reaction mixture was heated to 70° C. for 5 days. The title compound (650.0 mg, 98%) was isolated by chromatography (1-4% EtOAc-hexanes).

Workup

  1. customsparged with argon for 15 minutes
  2. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-d50764b2dbf34fb0a26460a392e567c7
Source dataset
uspto-grants-2003_03
Patent number
US06531599B2

Reaction notes

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