3-Aminopyridine → N-pyridin-3-ylpyridin-3-amine

HRID 563946

反応式

HRID 563946 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:3]=1

参加物

7

反応物 3

HCID 100093-AminopyridineHCID 122863-BromopyridineHCID 23676156Sodium t-butoxide

生成物 1

HCID 598775N-pyridin-3-ylpyridin-3-amine収率 84.4%

試薬・触媒・溶媒 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-bromopyridine (4.75 gm, 30 mmol) and 3-aminopyridine (1.88 gm, 20 mmol) in dry toluene (8 mL) was added sodium t-butoxide (2.3 gm, 24 mmol), tris(dibenylideneacetone) dipalladium(0) (63 mg, 0.069 mmol), and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (XANTPHOS) (183 mg, 0.317 mmol). The vessel was capped with a septum, degassed (3×), and heated at 100 C for ˜24 hours. The cooled reaction was diluted with methylene chloride, washed with NaHCO3 solution, water, and the organic layer dried over anhydrous sodium sulfate, filtered and the solvent concentrated to a small volume. Upon addition of diethyl ether and a few drops of methanol the product precipitated. After stirring this mixture for ˜15 hours the purified product was isolated by filtration to give 2.89 gm (84% yield) of the title compound.

後処理

  1. customThe vessel was capped with a septum
  2. customdegassed (3×)
  3. temperatureheated at 100 C for ˜24 hours
  4. customThe cooled reaction
  5. washwashed with NaHCO3 solution, water
  6. dry with materialthe organic layer dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe solvent concentrated to a small volume
  9. additionUpon addition of diethyl ether and a few drops of methanol the product
  10. customprecipitated
  11. customwas isolated by filtration

出典と根拠

ORDレコード
ord-33bd4cb3980b4265898ae7d7d3085f54
出典データセット
uspto-grants-2011_11
特許番号
US08067607B2

関連ノート

読み込み中…