Sodium Carbonate → 5'-bromospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

HRID 48506Notes

Reaction equation

HRID 48506 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][C:2]21[CH:14]1[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]1)[CH2:10]2.C([O-])(=O)C.[Na+].[Br:22]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Br:22][C:8]1[CH:9]=[C:4]2[CH2:3][C:2]3([CH:14]4[CH2:13][CH2:12][N:11]([CH2:16][CH2:15]4)[CH2:10]3)[O:1][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24408BromineHCID 517045Sodium AcetateHCID 9815800Spiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

Product 1

HCID 103571335'-bromospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]Yield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (100 mg, 0.462 mmol) and sodium acetate (410 mg, 5 mmol) in 50% aqueous acetic acid (4 mL) was heated to 60° C. Bromine (0.100 mL, 1.94 mmol) was added via a syringe over 10 minutes, and the solution was then heated under reflux for 1 hour. The mixture was allowed to cool to ambient temperature, basified to pH>10 with sodium carbonate, and extracted with chloroform (3×15 mL). The combined extracts were dried (MgSO4), filtered, and evaporated under reduced pressure to give the title compound (110 mg, 0.37 mmol, 81%) as an off-white solid: electrospray MS 295 ([MH]+, with 79Br, 100), 297 ([MH]+, with 81Br, 98).

Workup

  1. temperaturethe solution was then heated
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with chloroform (3×15 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f98f9e746fae47b7a342ac48c29221fc
Source dataset
uspto-grants-2004_03
Patent number
US06703502B2

Reaction notes

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