Methane → 4-bromo-1-(2-(methylthio)pyrimidin-4-yl)-1H-indole

HRID 41965

반응식

HRID 41965 반응식
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])C=1.C.C[N:24]1C(=O)CCC1>O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:18]1[CH:19]=[CH:14][N:24]=[C:16]([S:20][CH3:21])[N:17]=1

참가 물질

7

반응물 5

HCID 297MethaneHCID 13387N-methyl-2-pyrrolidone2회HCID 24758Sodium hydrideHCID 6764944-BromoindoleHCID 105349684-Chloro-2-(methylsulfanyl)pyridine

생성물 1

HCID 581379584-bromo-1-(2-(methylthio)pyrimidin-4-yl)-1H-indole

시약·촉매·용매 1

HCID 962Water용매

실험 절차

4-Bromoindole (20 g, 102 mmol) was dissolved in 70 mL of NMP and the solution was stirred under ice bath. Sodium hydride (6 g, 60% in mineral oil, 150 mmol) was added in small portions over 30 minutes. The mixture was stirred at room temperature for 40 minutes and then cooled under ice bath. A solution of 4-chloro-2-methylsulfanylpyridine (19.7 g, 122 mmol) in 10 mL of NMP was added through a dropping funnel over 10 minutes. The mixture was stirred at room temperature overnight. Water (150 mL) was added with stirring. The solid material was filtered and washed with water, air dried. This material was suspended in hot ethyl acetate (200 mL) and dichloromethane (200 mL) was added to give a clear solution. Charcoal (5 g) was added and the mixture was stirred for 10 minutes, filtered through Celite. The resulting solution was gently evaporated to remove dichloromethane until crystalline material appeared. The mixture was kept at room temperature for 2 hrs and crystals were filtered, rinsed with cold ethyl acetate (90 mL), air dried, to give 4-bromo-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indole as an off white solid (21.5 g, 65%). LC-MS calcd for C13H10BrN3S (m/e) 318.98, obsd 320.0 (M+H).

후처리

  1. stirringThe mixture was stirred at room temperature for 40 minutes
  2. temperaturecooled under ice bath
  3. stirringThe mixture was stirred at room temperature overnight
  4. stirringwith stirring
  5. filtrationThe solid material was filtered
  6. washwashed with water, air
  7. customdried
  8. additiondichloromethane (200 mL) was added
  9. customto give a clear solution
  10. stirringthe mixture was stirred for 10 minutes
  11. filtrationfiltered through Celite
  12. customThe resulting solution was gently evaporated
  13. customto remove dichloromethane until crystalline material
  14. filtrationcrystals were filtered
  15. washrinsed with cold ethyl acetate (90 mL), air
  16. customdried

출처 및 근거

ORD 기록
ord-a623f781302f4d5bacdf3d56b500ae41
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536172B2

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