Chloropyrazine → 2-(3-Isopropyl-phenyl)-pyrazine

HRID 965815ノート

反応式

HRID 965815 の反応式
[CH:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].Cl[C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1>C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]([C:14]2[CH:19]=[N:18][CH:17]=[CH:16][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 73277ChloropyrazineHCID 27734783-Isopropylbenzeneboronic acid

生成物 1

HCID 220371202-(3-Isopropyl-phenyl)-pyrazine

試薬・触媒・溶媒 2

HCID 2724231Bis(1,2-bis(diphenylphosphino)ethane)palladium(0)触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a solution of commercial 3-isopropyl-benzene boronic acid (1.0 g) in a 2:2:1 mixture of toluene/1M Na2CO3/EtOH (122 mL), at r.t., 2-chloropyrazine (599 μL) and the bis[1,2-bis(diphenylphosphino)ethane]-palladium(0) catalyst (110 mg) were added. The reaction mixture was heated at 80° C. for 3 hr. It was then cooled down and partitioned between AcOEt/sat.aq. NaCl. The phases were separated and the organic layer was dried. The solids were filtered and the solvent evaporated. The crude oil was purified by flash chromatography (CH/AcOEt 7:3) obtaining the title compound as a clear oil (468 mg).

後処理

  1. temperatureIt was then cooled down
  2. custompartitioned between AcOEt/
  3. customThe phases were separated
  4. customthe organic layer was dried
  5. filtrationThe solids were filtered
  6. customthe solvent evaporated
  7. customThe crude oil was purified by flash chromatography (CH/AcOEt 7:3)

出典と根拠

ORDレコード
ord-fb16094d8a864f63b200abc6fd9804a1
出典データセット
uspto-grants-2005_10
特許番号
US06951861B1

反応ノート

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