Trimethylsilylacetylene → HCID 178504177, compound

HRID 1793284Notes

Reaction equation

HRID 1793284 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[N:8]=[C:7]([OH:15])[C:6]([OH:16])=[N:5]2.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>CN(C)C=O.C(N(CC)CC)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:15][C:7]1[C:6]([OH:16])=[N:5][C:4]2[C:9](=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:2]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH:3]=2)[N:8]=1

Participants

8

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 178526419HCID 178526419, compound

Product 1

HCID 178504177HCID 178504177, compoundYield 70%

Reagents, catalysts & solvents 5

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 500 mg (1.9 mmol) 6-bromo-2,3-dihydroxy-7-nitroquinoxaline (supra) in 10 ml dry dimethylformamide and 20 ml dry triethylamine is added to 4 mg palladium(II)acetate, 8 mg triphenylphosphine and 600 μl (4.3 mmol) trimethylsilylacetylene. The mixture is refluxed for 2.5 h under nitrogen. After cooling to room temperature, the reaction mixture is evaporated in vacuo. The residue is stirred with water, filtered and washed with water to give 500 mg of a crude product. The crude product is dissolved in ethyl acetate and purified by column chromatography (silica gel) to give 400 mg (70%) of 2,3-dihydroxy-6-trimethylsilylethynyl-7-nitroquinoxaline. NMR (DMSO-d6): δ 7.8 (1H, s), δ 7.2 (1H, s), δ 0.3 (9H, s).

Workup

  1. temperatureThe mixture is refluxed for 2.5 h under nitrogen
  2. customthe reaction mixture is evaporated in vacuo
  3. filtrationfiltered
  4. washwashed with water
  5. customto give 500 mg of a crude product
  6. custompurified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-2b9757f8dd5e40beb81d93fb78750d32
Source dataset
uspto-grants-2006_07
Patent number
US07081346B2

Reaction notes

Loading…