2-(Tributylstannyl)pyrazine → HCID 24864396, compound

HRID 447010Notes

Reaction equation

HRID 447010 reaction equation
I[C:2]1[CH:3]=[C:4](I)[C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=1.C([Sn](CCCC)(CCCC)[C:23]1[CH:28]=[N:27][CH:26]=[CH:25][N:24]=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>[N:24]1[CH:25]=[CH:26][N:27]=[CH:28][C:23]=1[C:2]1[CH:3]=[C:4]([C:28]2[CH:23]=[N:24][CH:25]=[CH:26][N:27]=2)[C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=1

Participants

5

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 57813756HCID 57813756, compound

Product 1

HCID 24864396HCID 24864396, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-(5,7-diiodo-benzothiazol-2-yl)-3-ethyl-urea (0.50 g, 1.0 mmol) in DMF (5.0 mL) was added 2-tributylstannyl-pyrazine (0.78 g, 2.0 mmol) under nitrogen atmosphere at room temperature. The reaction mixture was degassed for half an hour followed by the addition of tetrakis(triphenylphosphine)palladium(0) (0.18 g, 0.10 mmol). The reaction mixture was again degassed for half an hour and then heated at 120° C. for 2 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), DMF was distilled off, added water and extracted with ethyl acetate (×3). The combined organic layer was dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The compound was purified by chromatography on silica (230-400 M) using ethyl acetate/Methanol) (95:5) to provide the title compound as off white solid (0.025 g, 6.5%).

Workup

  1. customThe reaction mixture was degassed for half an hour
  2. customThe reaction mixture was again degassed for half an hour
  3. customAfter the completion of the reaction (TLC monitoring), DMF
  4. distillationwas distilled off
  5. additionadded water
  6. extractionextracted with ethyl acetate (×3)
  7. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  8. customevaporated to dryness under reduced pressure
  9. customThe compound was purified by chromatography on silica (230-400 M)

Sources & evidence

ORD record
ord-69c3c35376c346f8aa904c707d7a3a95
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Reaction notes

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