HCID 72434529, compound → HCID 58817647, compound

HRID 2111752Notes

Reaction equation

HRID 2111752 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:18]2[S:19][CH:20]=[CH:21][C:22]=2Br)=[N:15][NH:16][CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>COC(O)C.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:18]3[S:19][CH:20]=[CH:21][C:22]=3[N:16]([CH3:17])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 72434529HCID 72434529, compound

Product 1

HCID 58817647HCID 58817647, compoundYield 93%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
70 °C

Procedure

4-[(3-Bromo-thiophen-2-yl)-(methyl-hydrazono)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (700 mg, 1.74 mmol) was mixed with CuI (20 mg), CsCO3 (650 mg, 1.15 eq) in methoxyethanol (10 mL). The mixture was heated to 70° C. for 2 hr. then stirred overnight at room temperature. The solvent was stripped on rotary evaporator. The residue was extracted into EtOAc then washed with brine and concentrated down to an oil. This oil was purified via chromatography (eluted with 0-10% MeOH in DCM) yielding 520 mg (68%) of the desired product.

Workup

  1. customThe solvent was stripped on rotary evaporator
  2. extractionThe residue was extracted into EtOAc
  3. washthen washed with brine
  4. concentrationconcentrated down to an oil
  5. customThis oil was purified via chromatography (eluted with 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-ddba7eee09d74e509abdf43f335df0cc
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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