2-(Tributylstannyl)pyrazine → HCID 68755976, compound

HRID 2098207Notes

Reaction equation

HRID 2098207 reaction equation
Br[C:2]1[C:3]([C:10]#[N:11])=[CH:4][S:5][C:6]=1[N+:7]([O-:9])=[O:8].C([Sn]([C:25]1[CH:30]=[N:29][CH:28]=[CH:27][N:26]=1)(CCCC)CCCC)CCC>O1CCOCC1.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+:7]([C:6]1[S:5][CH:4]=[C:3]([C:10]#[N:11])[C:2]=1[C:25]1[CH:30]=[N:29][CH:28]=[CH:27][N:26]=1)([O-:9])=[O:8]

Participants

5

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 591688104-Bromo-5-nitrothiophene-3-carbonitrile

Product 1

HCID 68755976HCID 68755976, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-bromo-5-nitrothiophene-3-carbonitrile (312 mg, 1.34 mmol) in dioxane (4 mL) was added tetrakis(triphenylphosphine)palladium(0) (154 mg, 0.133 mmol) and tributylstannylpyrazine (794 mg, 2.15 mmol). This was heated by microwave irradiation to 140° C. for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue purified by flash chromatography to afford the titled compound (166 mg, 53%): Rf=0.33 (20% EtOAc/hexanes; silica); HPLC method [4], retention time=1.45 min; MS (ESI) 233.0 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-709a39448b874ccda791d05aacbf3efd
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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