Dichloromethane → 6-[6-(1H-pyrazol-4-yl)-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-quinoline

HRID 15988

반응식

HRID 15988 반응식
[F-].[Cs+].Br[C:4]1[N:9]=[C:8]2[N:10]([CH2:13][C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[CH:19][CH:18]=[CH:17]4)[N:11]=[N:12][C:7]2=[N:6][CH:5]=1.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[N:34][N:35](C(OC(C)(C)C)=O)[CH:36]=2)O1.C(Cl)Cl>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].O.COCCOC>[NH:34]1[CH:33]=[C:32]([C:4]2[N:9]=[C:8]3[N:10]([CH2:13][C:14]4[CH:15]=[C:16]5[C:21](=[CH:22][CH:23]=4)[N:20]=[CH:19][CH:18]=[CH:17]5)[N:11]=[N:12][C:7]3=[N:6][CH:5]=2)[CH:36]=[N:35]1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 25953Cesium fluorideHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

생성물 1

HCID 248519536-[6-(1H-pyrazol-4-yl)-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-quinoline수율 63%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

A mixture of DME (3.0 mL) and 1 M aqueous CsF (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), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (95 mg, 0.32 mmol) and Pd(dppf)2Cl2.CH2Cl2 (6.1 mg, 0.01 mmol). The vial was capped and heated to 80° C. for 16 hours. Water (5 mL) was added to the crude reaction mixture and the resulting suspension was filtered. The precipitate was washed with water and air dried. The precipitate was purified by column chromatography using gradient elution with methanol and dichloromethane to afford 6-((6-(1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (60 mg, 62%).

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. customreaction mixture
  6. filtrationthe resulting suspension was filtered
  7. washThe precipitate was washed with water and air
  8. customdried
  9. customThe precipitate was purified by column chromatography
  10. washelution with methanol and dichloromethane

출처 및 근거

ORD 기록
ord-7f31b0d2072d4f86b3553365e5f36888
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732604B2

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