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

HRID 597997Notes

Reaction equation

HRID 597997 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+].[O:31]([C:38]1[CH:39]=[C:40](B(O)O)[CH:41]=[N:42][CH:43]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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>[O:31]([C:38]1[CH:39]=[C:40]([C:7]2[CH2:14][CH:13]3[CH2:15][CH:9]([CH2:10][N:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12]3)[CH:8]=2)[CH:41]=[N:42][CH:43]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 53401497(5-Phenoxypyridin-3-yl)boronic acidHCID 57486348Ethyl 7-(trifluoromethylsulfonyloxy)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate

Product 1

HCID 57486354Ethyl 7-(5-phenoxy-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylateYield 87%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
95 °C

Procedure

To a solution of ethyl 7-(trifluoromethylsulfonyloxy)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate (0.13 g, 0.38 mmol) in dimethoxyethane (3 mL) was added saturated sodium carbonate solution (1 mL), lithium chloride (0.04 g, 0.9 mmol) and 5-phenoxy-3-pyridinylboronic acid (0.17 g, 0.79 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 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), extracted with chloroform (3×5 mL). The 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 0-2% methanol in chloroform/as eluent, gave ethyl 7-(5-phenoxy-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate as a light yellow oil (0.12 g, 87%).

Workup

  1. customThe flask was alternately evacuated
  2. additionfilled with argon three times
  3. customThe flask was sealed under argon
  4. customthe stirred reaction mixture
  5. temperatureThe mixture was cooled to ambient temperature
  6. extractionextracted with chloroform (3×5 mL)
  7. dry with materialThe 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-691716a5eca2407db62d356867b2abe6
Source dataset
uspto-grants-2011_03
Patent number
US07897611B2

Reaction notes

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