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

HRID 551562노트

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HRID 551562 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5b423b6b34454a69b8d93b1648e200cd
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947711B2

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