2,6-Dibromopyridine → 6-Bromo-2,4'-bipyridine

HRID 1796086Notes

Reaction equation

HRID 1796086 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)CCC.[Br:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23](Br)[N:22]=1>O1CCCC1.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>[Br:20][C:21]1[N:22]=[C:23]([C:6]2[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=2)[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 122742,6-DibromopyridineHCID 27373184-(Tri-n-butylstannyl)pyridine

Product 1

HCID 135464536-Bromo-2,4'-bipyridineYield 53.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Tri-n-butylstannylpyridine (3.30 g, 8.9 mmol) was added to a degassed and stirred solution of 2,6-dibromopyridine (2.00 g, 8.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (5 mol %) in tetrahydrofuran (30 ml) under an atmosphere of nitrogen then heated to reflux for 48 h. Solvent was removed in vacuo and purification by chromatography on silica gel eluting with dichloromethane followed by trituration with isohexane gave 6-bromo-2,4′-bipyridinyl (1.05 g) as a white solid: δH (400 MHz, CDCl3) 7.52-7.57 (1H, m), 7.66-7.70 (1H, m), 7.86 (2H, m), 8.10-8.50 (1H, m), 8.72-8.76 (1H, m), 8.77-8.81 (1H, m); m/z (ES+) 234/236 (M++H).

Workup

  1. customa degassed
  2. temperaturethen heated
  3. temperatureto reflux for 48 h
  4. customSolvent was removed in vacuo and purification by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-425722a5bf5e4dd7b5bcff0e438ab9fd
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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