2,6-Dibromopyridine → 2-Bromo-6-(2,4,6-trimethylphenyl)pyridine

HRID 598104Notes

Reaction equation

HRID 598104 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1B(O)O.CC(C)([O-])C.[K+]>COCCOC.C(O)(C)(C)C.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:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:11]2[C:12]([CH3:17])=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=2[CH3:9])[N:3]=1

Participants

7

Reactant 3

HCID 122742,6-DibromopyridineHCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 714136972-Bromo-6-(2,4,6-trimethylphenyl)pyridineYield 68%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6386tert-ButanolSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

2,6-Dibromopyridine (9.47 g, 40 mmol) was dissolved in 80 mL of 1,2-dimethoxyethane (1,2-dimethoxyethane). Tetrakis(triphenylphosphine)palladium(0) (2.31 g, 2.00 mmol) was added and the mixture was heated at 50° C. for 15 min. The solution was cooled and 2,4,6-trimethylbenzeneboronic acid (6.56 g, 40 mmol) dissolved in 40 mL of 1,2 dimethoxyethane was added. Finally, potassium t-butoxide (8.97 g, 80 mmol) was added as a solution in 40 mL of t-butanol. The reaction was heated for 0.5 h at 90° C. The solution was cooled and filtered through celite. Flash chromatography (2% ethyl acetate/hexanes) gave 7.48 g (68% yield) of the title compound.

Workup

  1. temperatureThe solution was cooled
  2. additionwas added
  3. temperatureThe reaction was heated for 0.5 h at 90° C
  4. temperatureThe solution was cooled
  5. filtrationfiltered through celite

Sources & evidence

ORD record
ord-2783704e0ed34a58819241a63fb9a129
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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