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Potassium vinyltrifluoroborate → 1-((5-fluoropyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole

HRID 79477
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HRID 79477 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[C:11](I)=[N:10]2)=[N:6][CH:7]=1.[B-](F)(F)(F)[CH:23]=[CH2:24].[K+]>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].CC(O)C.C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[C:11]([CH:23]=[CH2:24])=[N:10]2)=[N:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 23679353Potassium vinyltrifluoroborateHCID 67261198HCID 67261198, 화합물

생성물 1

HCID 672598561-((5-fluoropyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 22597222Tetrahydrofuran 2-propanol용매

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온도
90 °C

실험 절차

A suspension of 1-((5-fluoropyridin-2-yl)methyl)-3-iodo-4-nitro-1H-indazole (0.968 g, 2.43 mmol) in 4:1 IPA/THF (10 mL) was degassed under argon. To the suspension was added TEA (0.678 mL, 4.86 mmol), potassium trifluoro(vinyl)borate (0.651 g, 4.86 mmol) and PdCl2(dppf)*dcm (0.199 g, 0.243 mmol). The mixture was then heated with stirring at 90° C. for 16 hours under argon. The mixture was allowed to cool, filtered through GF/F paper and concentrated under reduced pressure. The residue was dissolved in DCM and purified by chromatography on silica using a Biotage system, eluting with 1-10% Et2O in DCM. This gave 1-((5-fluoropyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole (229 mg).

후처리

  1. customwas degassed under argon
  2. temperatureThe mixture was then heated
  3. temperatureto cool
  4. filtrationfiltered through GF/F paper
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in DCM
  7. custompurified by chromatography on silica using a Biotage system
  8. washeluting with 1-10% Et2O in DCM

출처 및 근거

ORD 기록
ord-db8c01992de046a6bc3560eaf1848133
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841455B2

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