Sodium Carbonate → 4-(Pyridin-4-yl)naphth-1-ylamine

HRID 1936707

반응식

HRID 1936707 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[N:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([NH2:12])=[CH:4][CH:3]=2)=[CH:21][CH:20]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 753034-Bromo-1-naphthylamineHCID 2734379(Pyridin-4-yl)boronic acid

생성물 1

HCID 108570124-(Pyridin-4-yl)naphth-1-ylamine수율 78.7%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A stirred suspension of 4-bromonaphth-1-ylamine (10 g, 45 mmole) in 1,2-dimethoxyethane (400 ml) and water (100 ml) containing sodium carbonate (14 g) was flushed with argon for 0.3 hours. Tetrakis(triphenylphosphine) palladium (0) (2.75 g, 2.4 mmole) was added followed by pyridin-4-ylboronic acid (5.7 g, 46 mmole) and the mixture heated at reflux for 5 hours. The mixture was concentrated in vacuo to a brown slurry and partitioned between dichloromethane and water. The aqueous was further extracted with dichloromethane and the combined organics dried (Na2SO4) and concentrated in vacuo to a brown solid (13.2 g). Purification of the solid by flash chromatography eluting with ethyl acetate afforded the title compound as a yellow crystalline solid (7.8 g, 78%).

후처리

  1. customwas flushed with argon for 0.3 hours
  2. temperaturethe mixture heated
  3. temperatureat reflux for 5 hours
  4. concentrationThe mixture was concentrated in vacuo to a brown slurry
  5. custompartitioned between dichloromethane and water
  6. extractionThe aqueous was further extracted with dichloromethane
  7. dry with materialthe combined organics dried (Na2SO4)
  8. concentrationconcentrated in vacuo to a brown solid (13.2 g)
  9. customPurification of the solid by flash chromatography
  10. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-1870494c508f446d85291f9137834446
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06391891B1

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