Styrene → (S)-(+)-5'-(E)-(Phenylethenyl)spiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

HRID 841071Notes

Reaction equation

HRID 841071 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH2:10][C@@:9]3([CH:15]4[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]4)[CH2:11]3)[O:8][C:5]2=[N:6][CH:7]=1.[CH2:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:20]1(/[CH:19]=[CH:18]/[C:2]2[CH:3]=[C:4]3[CH2:10][C@@:9]4([CH:15]5[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]5)[CH2:11]4)[O:8][C:5]3=[N:6][CH:7]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 7501StyreneHCID 8471TriethylamineHCID 54506689HCID 54506689, compound

Product 1

HCID 18719786(S)-(+)-5'-(E)-(Phenylethenyl)spiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]Yield 55%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (S)-(+)-5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (150 mg, 0.51 mmol), styrene (0.07 mL, 0.61 mmol), palladium(II)acetate (1.2 mg, 0.0053 mmol), tri-o-tolylphosphine (6.4 mg, 0.021 mmol), and triethylamine (0.5 mL, 3.6 mmol) in anhydrous acetonitrile (0.5 mL), in a heavy-walled threaded glass tube containing a magnetic stir bar, was purged with argon and sealed with a Teflon plug and FETFE O-ring. The mixture was stirred and heated at 100° C. for 2 hours, cooled to room temperature, dissolved in chloroform (10 mL), washed with saturated aqueous sodium carbonate (1 mL), dried (MgSO4), and evaporated under reduced pressure. Recrystallization from ethyl acetate afforded the title compound (90 mg, 0.28 mmol, 55%) as a light tan solid: electrospray MS (m/z, relative intensity) 319 ([MH]+, 100).

Workup

  1. customwas purged with argon
  2. customsealed with a Teflon plug and FETFE O-ring
  3. temperaturecooled to room temperature
  4. dissolutiondissolved in chloroform (10 mL)
  5. washwashed with saturated aqueous sodium carbonate (1 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-54591f55454e4d96ad4447d1d2340a10
Source dataset
uspto-grants-2002_04
Patent number
US06369224B1

Reaction notes

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