2-(Tributylstannyl)pyrazine → HCID 70557130, compound

HRID 1427158Notes

Reaction equation

HRID 1427158 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]([O:10][CH3:11])=[O:9].C([Sn](CCCC)(CCCC)[C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=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>[N:18]1[CH:19]=[CH:20][N:21]=[CH:22][C:17]=1[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 12574055Methyl 4-chloronicotinate2×

Product 1

HCID 70557130HCID 70557130, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 4-chloro-3-pyridinecarboxylate (1200 mg; may be prepared as described in Intermediate 18) and 2-(tributylstannanyl)pyrazine (3000 mg) in toluene (20 mL), tetrakis(triphenylphosphine)palladium(0) (808 mg) in toluene (20 mL) was added and the reaction mixture was stirred at 100° C. for 3 h. Then the solvent was evaporated in vacuo and the crude product was added to a silica gel column and eluted with cyclohexane/EtOAc/MeOH=7/2.5/0.5. The evaporation of the collected fractions gave 1 g of the title compound as a white solid.

Workup

  1. customThen the solvent was evaporated in vacuo
  2. additionthe crude product was added to a silica gel column
  3. washeluted with cyclohexane/EtOAc/MeOH=7/2.5/0.5
  4. customThe evaporation of the collected fractions

Sources & evidence

ORD record
ord-3626be6e62c84e0496a9463ee19f9fe7
Source dataset
uspto-grants-2015_01
Patent number
US08933132B2

Reaction notes

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