Trimethylsilylacetylene → HCID 68960082, compound

HRID 1784948Notes

Reaction equation

HRID 1784948 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>C(N(CC)CC)C>[CH3:17][Si:18]([C:21]#[C:22][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 11033439tert-Butyl 3-bromobenzylcarbamate

Product 1

HCID 68960082HCID 68960082, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

To tert-butyl 3-bromobenzylcarbamate (220 mg, 1 mmol) in triethylamine (3 ml), trimethylsilyl acetylene (147 mg, 1.5 mmol) was added followed by cuprous iodide (8 mg, 0.04 mmol). After stirring for 5 min, dichloro bis (triphenylphosphine) palladium (II) (35 mg, 0.05 mmol) was added and the reaction mixture was heated at 90° C. for 18 h. Then the reaction mixture was filtered, diluted with ethyl acetate and washed with water. Organic layer was dried, evaporated and the crude residue was purified by column chromatography to obtain tert-butyl 3-((trimethylsilyl)ethynyl)benzylcarbamate in 67% yield.

Workup

  1. filtrationThen the reaction mixture was filtered
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. customOrganic layer was dried
  5. customevaporated
  6. customthe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-5eef4eb17fbb40088589f2c56bbf1698
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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