Sodium Carbonate → Ethyl 7-(5-phenyl-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate

HRID 749144Notes

Reaction equation

HRID 749144 reaction equation
FC(F)(F)S(O[C:7]1[CH2:14][CH:13]2[CH2:15][CH:9]([CH2:10][N:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12]2)[CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+].[C:31]1([C:37]2[CH:38]=[C:39](B(O)O)[CH:40]=[N:41][CH:42]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:31]1([C:37]2[CH:38]=[C:39]([C:7]3[CH2:14][CH:13]4[CH2:15][CH:9]([CH2:10][N:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12]4)[CH:8]=3)[CH:40]=[N:41][CH:42]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 45790037(5-Phenylpyridin-3-yl)boronic acidHCID 57486348Ethyl 7-(trifluoromethylsulfonyloxy)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate

Product 1

HCID 57486353Ethyl 7-(5-phenyl-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylateYield 98.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of ethyl 7-(trifluoromethylsulfonyloxy)-3-azabicyclo[3.3.1] non-6-ene-3-carboxylate (0.12 g, 0.35 mmol) in dimethoxyethane (3 mL) was added saturated sodium carbonate solution (1 mL), lithium chloride (0.04 g, 0.9 mmol) and 5-phenyl-3-pyridinylboronic acid (0.12 g, 0.7 mmol). The flask was alternately evacuated and filled with argon three times. Then tetrakis(triphenylphosphine)palladium(0) (0.01 g, 0.01 mmol) was added, and the evacuation and argon fill was performed once again. The flask was then sealed under argon, and the stirred reaction mixture was heated at 95(C for 2 h. The mixture was cooled to ambient temperature, diluted with water (10 mL) and extracted with chloroform (3×5 mL). The combined extracts were dried over sodium sulfate and filtered. Concentration of the filtrate by rotary evaporation, followed by purification of the residue by silica gel column chromatography, using a gradient of chloroform/methanol (0-2% methanol) as eluent, gave ethyl 7-(5-phenyl-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate as a light yellow oil (0.12 g, 90%).

Workup

  1. customThe flask was alternately evacuated
  2. additionfilled with argon three times
  3. customThe flask was then sealed under argon
  4. customthe stirred reaction mixture
  5. temperaturewas heated at 95(C for 2 h
  6. extractionextracted with chloroform (3×5 mL)
  7. dry with materialThe combined extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. customConcentration of the filtrate by rotary evaporation
  10. customfollowed by purification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-aa863c751a844839ae5e90cddf19ed49
Source dataset
uspto-grants-2008_07
Patent number
US07402592B2

Reaction notes

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