2-(Tributylstannyl)-1,3-thiazole → 4-(1-Phenyl-1-(thiazol-2-yl)-methylene)-piperidine-1-carboxylic Acid tert-butyl Ester

HRID 1394419Notes

Reaction equation

HRID 1394419 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14](Br)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:27]1[S:28][CH:29]=[CH:30][N:31]=1)CCC>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:27]2[S:28][CH:29]=[CH:30][N:31]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 590345854-(1-Bromo-1-phenyl-methylene)-piperidine-1-carboxylic Acid tert-butyl Ester

Product 1

HCID 670467134-(1-Phenyl-1-(thiazol-2-yl)-methylene)-piperidine-1-carboxylic Acid tert-butyl EsterYield 94.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-(1-bromo-1-phenyl-methylene)-piperidine-1-carboxylic acid tert-butyl ester (0.205 g, 0.58 mmol) and 2-(tri-n-butylstannyl)thiazole (0.239 g, 0.64 mmol) in 6 mL of dry DMF was degassed with a stream of Ar bubbles for 10 min. To this solution was added (Ph3P)4Pd (0.067 g, 10 mol %) and CuI (0.011 g, 10 mol %), and then the reaction vessel was sealed and heated at 90° C. for 18 h. The cooled mixture was concentrated and then it was partitioned with EtOAc-water. The organic phase was washed (brine), dried (MgSO4) and evaporated. Flash chromatography of the residue (SiO2/hexane-EtOAc, 3:2) afforded the title compound (0.195 g, 94%) as a yellow solid:

Workup

  1. customthe reaction vessel was sealed
  2. concentrationThe cooled mixture was concentrated
  3. customit was partitioned with EtOAc-water
  4. washThe organic phase was washed (brine)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-953ea685c23d458f8bfe934ce3a7b20b
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

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