2-(Tributylstannyl)pyrazine → 2-{3-[(Pyridin-4-yl)ethynyl]phenyl}pyrazine

HRID 271111Notes

Reaction equation

HRID 271111 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:21]1[CH:26]=[N:25][CH:24]=[CH:23][N:22]=1)CCC>C1(C)C=CC=CC=1.CCOC(C)=O.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:13]1[CH:14]=[CH:15][C:10]([C:9]#[C:8][C:4]2[CH:3]=[C:2]([C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)[CH:7]=[CH:6][CH:5]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 598345694-[(3-Bromophenyl)ethynyl]pyridine

Product 1

HCID 598345802-{3-[(Pyridin-4-yl)ethynyl]phenyl}pyrazineYield 40%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[(3-bromophenyl)ethynyl]pyridine (387 mg, 1.50 mmol) in toluene (10 mL) is added tetrakis(triphenylphosphine)palladium (87 mg, 0.075 mmol) and 2-(tributylstannyl)pyrazine (1.45 g, 3.75 mmol) at room temperature. After refluxing for 24 h, the reaction mixture is cooled and diluted with EtOAc (100 mL), washed with saturated NaHCO3 (2×30 mL), brine (30 mL), dried over MgSO4 and concentrated on a rotary evaporator. The crude material is purified by chromatography (silica gel, EtOAc/hexane: 40/60 to give the title compound (153 mg, 40%) as solid. mp: 94-95° C. MS(+) ES: 258 (M+OH)+.

Workup

  1. temperatureAfter refluxing for 24 h
  2. temperaturethe reaction mixture is cooled
  3. washwashed with saturated NaHCO3 (2×30 mL), brine (30 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated on a rotary evaporator
  6. customThe crude material is purified by chromatography (silica gel, EtOAc/hexane

Sources & evidence

ORD record
ord-183c21184ee54a64b188b5522dfd30e8
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

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