2-(Tributylstannyl)-1,3-thiazole → HCID 22678636, compound

HRID 1837731Notes

Reaction equation

HRID 1837731 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]3[C:19](OS(C(F)(F)F)(=O)=O)=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.C([Sn](CCCC)(CCCC)[C:37]1[S:38][CH:39]=[CH:40][N:41]=1)CCC>C1(C)C=CC=CC=1.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>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][CH2:17][C:18]3[C:19]([C:37]4[S:38][CH:39]=[CH:40][N:41]=4)=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:14][CH2:15]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 22678290HCID 22678290, compound

Product 1

HCID 22678636HCID 22678636, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

150 mg of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-[2-[((trifluoromethyl)sulfonyl]oxy]-3-pyridyl]ethyl]piperidine, 180 mg of 2-(tributylstannyl)thiazole and 20 mg of tetrakis(triphenylphosphine)palladium were suspended in 4 ml of toluene, and the mixture was heated under reflux for 2 hours under nitrogen flow. The solvent was evaporated, and the residue was purified by NH form silica gel column chromatography (ethyl acetate:hexane=1:4), to give 39 mg of the title compound as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours under nitrogen flow
  3. customThe solvent was evaporated
  4. customthe residue was purified by NH
  5. customform silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-7372a8696a7145489f9a9a0c744e71af
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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