HCID 58817653, compound → HCID 58817563, compound

HRID 2111748Notes

Reaction equation

HRID 2111748 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[C:12]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:13]=3[S:14][C:15]=2C(O)=O)[CH2:7][CH2:6]1)=[O:4]>N1C2C(=CC=CC=2)C=CC=1.CCOC(C)=O.[Cu]>[CH3:1][O:2][C:3]([N:5]1[CH2:6][CH2:7][CH:8]([C:11]2[C:12]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][C:13]=3[S:14][CH:15]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

5

Reactant 1

HCID 58817653HCID 58817653, compound

Product 1

HCID 58817563HCID 58817563, compoundYield 82.4%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 7047QuinolineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4-(2-carboxy-6-trifluoromethyl-benzo[b]thiophen-3-yl)-piperidine-1-carboxylic acid methyl ester (4.3 g, 11.1 mmol) and copper (705 mg, 11.1 mmol) in quinoline (28 mL) was heated at 200° C. for 45 minutes. Upon cooling to room temperature the mixture was diluted with EtOAc (50 mL) and filtered. The filtrate was washed with 5% HCl (2×20 mL), water (20 mL) and brine (20 mL), dried (MgSO4), filtered and evaporated. The residue was separated via chromatography (30% EtOAc in heptane) yielding 3.14 g (82%) of the desired product as a white solid.

Workup

  1. temperatureUpon cooling to room temperature the mixture
  2. filtrationfiltered
  3. washThe filtrate was washed with 5% HCl (2×20 mL), water (20 mL) and brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was separated via chromatography (30% EtOAc in heptane)

Sources & evidence

ORD record
ord-0767b4c8fcf14bdebd549438d27bc82f
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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