1,2-Dimethoxyethane → 6-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

HRID 15987

반응식

HRID 15987 반응식
COCCOC.C([O-])([O-])=O.[Na+].[Na+].Br[C:14]1[N:19]=[C:18]2[N:20]([CH2:23][C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[CH:29][CH:28]=[CH:27]4)[N:21]=[N:22][C:17]2=[N:16][CH:15]=1.[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1B(O)O>ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:14]1[N:19]=[C:18]2[N:20]([CH2:23][C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[CH:29][CH:28]=[CH:27]4)[N:21]=[N:22][C:17]2=[N:16][CH:15]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

생성물 1

HCID 593418296-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline수율 74.5%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
80 °C

실험 절차

A mixture of DME (3.0 mL) and 1 M aqueous Na2CO3 (0.88 mL) was degassed by bubbling in Argon for 10 minutes. The mixture was transferred via syringe to a vial containing 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (100 mg, 0.29 mmol), 2-fluorophenylboronic acid (45 mg, 0.32 mmol) and Pd(dppf)2Cl2.CH2Cl2 (6.2 mg, 0.01 mmol). The vial was capped and heated to 80° C. for 3.5 hours. The crude reaction mixture was diluted with dichloromethane then washed with water. The dichloromethane was dried over Na2SO4, filtered and concentrated by rotary evaporation. The residue was purified by column chromatography using gradient elution with ethyl acetate and dichloromethane to afford 6-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (77 mg, 74%).

후처리

  1. customwas degassed
  2. customby bubbling in Argon for 10 minutes
  3. customThe mixture was transferred via syringe
  4. customThe vial was capped
  5. customThe crude reaction mixture
  6. washthen washed with water
  7. dry with materialThe dichloromethane was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation
  10. customThe residue was purified by column chromatography
  11. washelution with ethyl acetate and dichloromethane

출처 및 근거

ORD 기록
ord-809f753e12c145829877418314079bb0
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732604B2

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