HCID 72434555, compound → HCID 58817532, compound

HRID 2111753Notes

Reaction equation

HRID 2111753 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:22]2[S:23][CH:24]=[CH:25][C:26]=2Br)=[N:15][NH:16][CH2:17][C:18]([F:21])([F:20])[F:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>COC(O)C.CCOC(C)=O.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[S:23][CH:24]=[CH:25][C:26]=3[N:16]([CH2:17][C:18]([F:21])([F:20])[F:19])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 72434555HCID 72434555, compound

Product 1

HCID 58817532HCID 58817532, compoundYield 104.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 30156371-MethoxyethanolSolvent

Conditions

Temperature
75 °C

Procedure

4-{(3-Bromo-thiophen-2-yl)-[(2,2,2-trifluoro-ethyl)-hydrazono]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (2.34 g, 4.98 mmol) was mixed with CuI (50 mg). CsCO3 (1.9 g, 1.2 eq) in methoxyethanol (25 mL). The mixture was heated to 75° C. for 1 hour. The mixture was then diluted with EtOAc and filtered. The filtrate was evaporated and the residue was purified via chromatography (eluted with 0-10% MeOH in DCM) yielding 2.03 g (>95%) of the desired product.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customthe residue was purified via chromatography (eluted with 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-f0dd3f65e6494c878b6ce2543ee3f0b5
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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