HCID 13545447, compound → HCID 10519842, compound

HRID 1161995Notes

Reaction equation

HRID 1161995 reaction equation
Br[C:2]1[C:7]([N+]([O-])=O)=[CH:6][CH:5]=[C:4]([Br:11])[C:3]=1[OH:12].C[Si]([C:17]#[C:18][C:19]1([OH:27])[CH:24]2[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1)(C)C>N1C=CC=CC=1>[Br:11][C:4]1[C:3]2[O:12][C:18]([C:19]3([OH:27])[CH:24]4[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]4)[CH2:20]3)=[CH:17][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 13545447HCID 13545447, compoundHCID 66893927HCID 66893927, compound

Product 1

HCID 10519842HCID 10519842, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,6-Dibromonitrophenol (3.0 g, 0.0119 mol), 3-[(trimethylsilyl)ethynyl]quinuclidin-3-ol (2.66 g, 0.0119 mol; obtained in Step 1), Cu2O (1.70 g, 0.0119 mol) and pyridine (200 mL) were added to a round bottom flask. The resulting mixture was heated at reflux overnight, filtered through Celite, and the solvent was evaporated. The residue was purified by chromatography on silica gel using ethyl acetate (250 mL) and methanol (500 mL) as eluents. The methanol fraction was evaporated to yield 1.12 g (29%) of the title compound. HPLC purity=90%, m/z=322 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered through Celite
  4. customthe solvent was evaporated
  5. customThe residue was purified by chromatography on silica gel
  6. customThe methanol fraction was evaporated

Sources & evidence

ORD record
ord-8a10edb416ba40f39f1b3fc59b7ff781
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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