Methyl 8-chloro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylate → Methyl 8-chloro-7-fluoro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylate

HRID 910153Notes

Reaction equation

HRID 910153 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[C:4](=[O:16])[CH:3]=1.[B-](F)(F)(F)[F:18].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CN(C=O)C>[Cl:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[C:4](=[O:16])[C:3]=1[F:18]

Participants

4

Reactant 2

HCID 817846Methyl 8-chloro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylateHCID 2724933Selectfluor

Product 1

HCID 57689813Methyl 8-chloro-7-fluoro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylateYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Methyl 8-chloro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylate (7b, 1.23 g, 5.1 mmol, 1 eq) was dissolved in DMF (10 ml) at 88° C. Selectfluor (3.61 g, 10.2 mmol, 2 eq) in DMF (10 ml) was added drop wise and the mixture heated for 2 hours. After concentration in vacuo the residue was purified by flash chromatography using 20-70% EtOAc/Hexane as eluent to give the title compound as an off-white solid (600 mg, 45%). [M+H] calc'd for C11H11ClFNO3, 260. found, 260

Workup

  1. temperaturethe mixture heated for 2 hours
  2. concentrationAfter concentration in vacuo the residue
  3. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-3cc29f8d70a3412da177b0704bc0ea63
Source dataset
uspto-grants-2011_09
Patent number
US08022057B2

Reaction notes

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