Hydrochloric Acid → (+/-)-Ethyl 1-bromo-3-fluoro-9-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indole-8-carboxylate

HRID 857422Notes

Reaction equation

HRID 857422 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:20]([O:22]C)=O)[N:6]2[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].CC(C)([O-])C.[K+].Cl>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]1[C:20](=[O:22])[CH:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:12][N:6]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21867557Ethyl 4-bromo-6-fluoro-2-(methoxycarbonyl)-1H-indole-1-butanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 91562839(+/-)-Ethyl 1-bromo-3-fluoro-9-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indole-8-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the compound of Step 1 (13.2 g, 34.1 mmol) in THF (100 mL) at 0° C. was added potassium t-butoxide (34.1 mmol, 1M THF solution). The mixture was stirred at 0° C. for 2 h, poured into 1N HCl and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and swished in EtOAc to give 11.6 g of the title compound.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3dda87754c32440bb9e7b83e38c96e51
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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