Triethylamine → 2-(2-((Trimethylsilyl)ethynyl)phenyl)acetamide

HRID 1778952Notes

Reaction equation

HRID 1778952 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH2:11])=[O:10].CCN(CC)CC.[C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])#[CH:20]>CN(C=O)C.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.[Cu]I>[CH3:22][Si:21]([C:19]#[C:20][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH2:11])=[O:10])([CH3:24])[CH3:23]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 184740882-(2-Iodophenyl)acetamide

Product 1

HCID 867126222-(2-((Trimethylsilyl)ethynyl)phenyl)acetamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(2-iodophenyl)acetamide (I6) (12.91 g, 49.52 mmol), Et3N (26 mL), ethynyltrimethylsilane (9.08 mL, 64.3 mmol), PdCl2(PPh3)2 (0.347 g, 0.495 mmol) and CuI (0.188 g, 0.989 mmol) in DMF (44 mL) was stirred under a nitrogen atmosphere at 50° C. for 3 hours. The volatiles were removed in vacuo and the resulting residue partitioned between EtOAc (100 mL) and water. The aqueous phase was extracted with EtOAc (3×50 mL), then the combined organic extracts were washed with water (3×70 mL), brine, dried (MgSO4), filtered and evaporated in vacuo to give the title compound I7 as a brown solid (11.4 g, 99%); 1H NMR (300 MHz, d6-DMSO) δ 7.40 (d, J=7.5 Hz, 1H), 7.20-7.36 (m, 4H), 6.94 (brs, 1H), 3.58 (s, 2H), 0.24 (s, 9H). LCMS-B: rt 6.884 min; m/z 232 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue partitioned between EtOAc (100 mL) and water
  3. extractionThe aqueous phase was extracted with EtOAc (3×50 mL)
  4. washthe combined organic extracts were washed with water (3×70 mL), brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-03abc6fd78144f7d92b2b93de5c610e2
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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