3-(Tributylstannyl)pyridine → HCID 18182435, compound

HRID 1359427Notes

Reaction equation

HRID 1359427 reaction equation
[CH2:1]([C:8]1[N:9]=[C:10](I)[S:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Sn](CCCC)(CCCC)CCCC)[CH:15]=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.C1(C)C(C)=CC=CC=1>[CH2:1]([C:8]1[N:9]=[C:10]([C:16]2[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=2)[S:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 34838483-(Tributylstannyl)pyridineHCID 18182210HCID 18182210, compound

Product 1

HCID 18182435HCID 18182435, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

5 ml of xylene was added to a mixture of 468 mg of 4-benzyl-2-iodothiazole, 580 mg of (3-pyridyl)tributyltin and 90 mg of tetrakis(triphenylphosphine)palladium(0), followed by heating under stirring at 150° C. in an oil bath for 2.5 hours. After cooling as it was, insoluble matters were filtered off through Celite and the solvent was removed. The residue was subjected to silica gel column chromatography using 20-25% ethyl acetate/hexane as an eluent for separation and purification, to give 101 mg of the target compound.

Workup

  1. temperatureby heating
  2. temperatureAfter cooling as it
  3. filtrationinsoluble matters were filtered off through Celite
  4. customthe solvent was removed
  5. customfor separation and purification

Sources & evidence

ORD record
ord-4c62a3140d0f4c42b17eb43382252e1d
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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