Potassium Carbonate → 6-[(E)-2-Phenylethenyl][1,2,5]thiadiazolo[3,4-b]pyridine

HRID 1943231Notes

Reaction equation

HRID 1943231 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]2=[N:8][S:9][N:10]=[C:4]2[CH:3]=1.[C:11]1(/[CH:17]=[CH:18]/B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>O>[C:11]1(/[CH:17]=[CH:18]/[C:2]2[CH:7]=[N:6][C:5]3=[N:8][S:9][N:10]=[C:4]3[CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 3616936-Bromo[1,2,5]thiadiazolo[3,4-b]pyridineHCID 5702628Styrylboronic acid

Product 1

HCID 685963166-[(E)-2-Phenylethenyl][1,2,5]thiadiazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 6-bromo[1,2,5]thiadiazolo[3,4-b]pyridine (for a preparation see Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1979), 17B(1), 13-16) (1.9 g, 8.79 mmol), [(E)-2-phenylethenyl]boronic acid (1.561 g, 10.55 mmol) and tetrakistriphenylphosphine palladium(0) (0.508 g, 0.440 mmol) was added 1,4-dioxane (38 ml) and then potassium carbonate (1.276 g, 9.23 mmol) in water (19 ml). The reaction was then stirred at reflux for 1.5 hours. The cooled reaction was partitioned between chloroform and water. The phases were separated with a hydrophobic frit and the organic extracts concentrated to give a black solid/gum (˜2.4 g). This crude material was purified by chromatography on silica eluting with 20-50% EtOAc in cyclohexane to give the product as a yellow/brown solid (0.88 g).

Workup

  1. temperatureat reflux for 1.5 hours
  2. customThe cooled reaction
  3. customwas partitioned between chloroform and water
  4. customThe phases were separated with a hydrophobic frit
  5. concentrationthe organic extracts concentrated

Sources & evidence

ORD record
ord-6ac3c1d9c72b4e2ab350ab1da417ab32
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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