Tributylvinyltin → HCID 22478918, compound

HRID 252746Notes

Reaction equation

HRID 252746 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.[CH2:15]([Sn](CCCC)(CCCC)C=C)[CH2:16]CC>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>[NH2:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:5]=[C:6]([CH:15]=[CH2:16])[N:7]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 5137221HCID 5137221, compound

Product 1

HCID 22478918HCID 22478918, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 221 (358 mg, 1.68 mmol) in dry toluene (7 mL) was added tributyl(vinyl)tin (514 μL, 1.76 mmol) followed by Pd(PPh3)4 (97 mg, 0.084 mmol) and the reaction mixture was heated at 100° C. for 16 h in a sealed tube. Then, the reaction mixture was allowed to cool to room temperature, concentrated, and purified directly by flash chromatography on silica gel (AcOEt/hexane: 10/90→430/70) to afford the title compound 222 (containing tributyltin chloride).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated
  3. custompurified directly by flash chromatography on silica gel (AcOEt/hexane: 10/90→430/70)

Sources & evidence

ORD record
ord-cd322c10f5204b44b3db05953f0862af
Source dataset
uspto-grants-2011_01
Patent number
US07868204B2

Reaction notes

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