Lithium Chloride → 3-Bromo-7-[2-ethoxyvinyl]-1,5-naphthyridine

HRID 273241ノート

反応式

HRID 273241 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[C:7]([Br:12])[CH:6]=2.C([Sn](CCCC)(CCCC)[CH:18]=[CH:19][O:20][CH2:21][CH3:22])CCC.[Li+].[Cl-].[F-].[K+]>C1(C)C=CC=CC=1.C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[N:4][CH:3]=[C:2]([CH:18]=[CH:19][O:20][CH2:21][CH3:22])[CH:11]=2

参加物

8

反応物 4

HCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 12366583,7-Dibromo-1,5-naphthyridineHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)ethene

生成物 1

HCID 670823433-Bromo-7-[2-ethoxyvinyl]-1,5-naphthyridine収率 55%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 3,7-dibromo-1,5-naphthyridine (0.5 g, 1.74 mmol), tributyl-2-ethoxy-vinylstannane (1.91 mmol, 0.69 g), LiCl (8.7 mmol, 0.37 g) and 0.085 g of PdCl2(PPh3)2 in 50 mL of toluene was heated at 95° C. for 16 hr. After cooling off, 20 mL of a 2 M solution of KF was added to the mixture and stirring was continued for 0.5 hr. The mixture was diluted with 100 mL of CH2Cl2 and washed successively with a saturated solution of sodium bicarbonate, brine and water. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was chromatographed using 5% MeOH in CH2Cl2 to give the desired material in 55% yield. 1H NMR (CDCl3, 300 MHz) δ 1.40 (m, 3H), 4.05 (m, 2H), 5.85 (s, 1H), 7.25 (s, 1H), 8.15 (m, 1H), 8.55 (m, 1H), 8.85 (m, 2H). MS (ESI) [M+H]+ at 280.

後処理

  1. temperatureAfter cooling off
  2. washwashed successively with a saturated solution of sodium bicarbonate, brine and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed

出典と根拠

ORDレコード
ord-8d80b49db92246b7aecd4cc2c5ec4b31
出典データセット
uspto-grants-2008_11
特許番号
US07456196B2

反応ノート

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