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

HRID 1943231ノート

反応式

HRID 1943231 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6ac3c1d9c72b4e2ab350ab1da417ab32
出典データセット
uspto-grants-2013_03
特許番号
US08389524B2

反応ノート

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