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

HRID 1936707

反応式

HRID 1936707 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1870494c508f446d85291f9137834446
出典データセット
uspto-grants-2002_05
特許番号
US06391891B1

関連ノート

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