Sodium Carbonate → 6-(2-Fluorophenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid

HRID 1696303Notes

Reaction equation

HRID 1696303 reaction equation
FC(F)(F)S(O[C:7]1[C:8](=[O:20])[N:9]2[C:13](=[C:14]([C:16](=[O:19])CC)[CH:15]=1)[CH2:12][CH2:11][CH2:10]2)(=O)=O.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C([O-])([O-])=[O:34].[Na+].[Na+]>C1(C)C=CC=CC=1.CCO>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:7]1[C:8](=[O:20])[N:9]2[C:13](=[C:14]([C:16]([OH:19])=[O:34])[CH:15]=1)[CH2:12][CH2:11][CH2:10]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 866140165-Oxo-8-propionyl-1,2,3,5-tetrahydroindolizin-6-yl trifluoromethanesulfonate

Product 1

HCID 668448276-(2-Fluorophenyl)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acidYield 64%

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-oxo-8-propionyl-1,2,3,5-tetrahydroindolizin-6-yl trifluoromethanesulfonate (0.10 g, 0.292 mmol), 2-fluorophenylboronic acid (0.050 g, 0.38 mmol), and 2M Na2CO3 (0.75 mL, 1.46 mmol) in toluene/EtOH (4 mL, 4:1) was heated at 160° C. for 30 min. in a Microwave Synthesizer. The mixture was cooled, and the layers were separated. The aqueous layer was acidified and the precipitate was filtered and air dried to afford the title compound (0.051 g, 64%). MS (m/z, M+1): 274.1.

Workup

  1. temperatureThe mixture was cooled
  2. customthe layers were separated
  3. filtrationthe precipitate was filtered
  4. customair dried

Sources & evidence

ORD record
ord-d02421a38de44ea5960caa6d3008ee4f
Source dataset
uspto-grants-2012_04
Patent number
US08163766B2

Reaction notes

Loading…