N-bromobutanimide → 10-Bromo-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

HRID 573283Notes

Reaction equation

HRID 573283 reaction equation
[N:1]1[C:6]2[CH:7]=[C:8]3[N:13]([C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH2:12][CH2:11][CH2:10][CH2:9]3.C1C(=O)N([Br:21])C(=O)C1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:21][C:7]1[C:6]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[N:13]2[C:8]=1[CH2:9][CH2:10][CH2:11][CH2:12]2

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 667277726,7,8,9-Tetrahydropyrido[2,3-b]indolizine

Product 1

HCID 6672788310-Bromo-6,7,8,9-tetrahydropyrido[2,3-b]indolizineYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6,7,8,9-tetrahydropyrido[2,3-b]indolizine (170 mg) in DMF (3 mL) was added NBS (193 mg) at 0° C. The mixture was stirred at 0° C. for 30 min. The mixture was added saturated NaHCO3 aqueous solution at 0° C. and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (217 mg).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-1f2857067d2342888e4afa93d4e455e3
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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