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

HRID 563946

반응식

HRID 563946 반응식
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

참가 물질

7

반응물 3

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

생성물 1

HCID 598775N-pyridin-3-ylpyridin-3-amine수율 84.4%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-33bd4cb3980b4265898ae7d7d3085f54
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067607B2

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