Nitrogen → 6-Bromo-2,4'-bipyridine

HRID 566708Notes

Reaction equation

HRID 566708 reaction equation
N#N.Br[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[N:5]=1.[N:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(Cl)Cl>C([O-])([O-])=O.[Na+].[Na+].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>[Br:10][C:6]1[N:5]=[C:4]([C:14]2[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=2)[CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 6344DichloromethaneHCID 122742,6-DibromopyridineHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 135464536-Bromo-2,4'-bipyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Procedure

Dry N2 was bubbled through a stirred solution of 2,6-dibromopyridine (1.6 gm, 6.7 mmole), pyridine-4-boronic acid (317 mg, 2.6 mmol), and Pd(PPh3)4 (160 mg) in aqueous 2M Na2CO3 (8 mL) and toluene (8 mL) at rt for 20 min. The reaction mixture was then heated to reflux for 10 hr. After cooling to rt CH2Cl2 (100 mL) was added and the mixture was washed with brine and dried (Na2SO4). Purification (Sio2, CH2Cl2/MeOH/NH4OH: 100/11/8) gave 6-bromo-[2,4′]bipyridine. MS (m/z): Calcd. C10H7N2Br (M+): 235, found: 234.9.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 10 hr
  3. additionwas added
  4. washthe mixture was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customPurification (Sio2, CH2Cl2/MeOH/NH4OH: 100/11/8)

Sources & evidence

ORD record
ord-b254e70807be48a7a00096807419b47f
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

Loading…