Dichloromethane → 3-(4-Fluorophenyl)-5-nitro-1H-indazole

HRID 227699노트

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HRID 227699 반응식
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4](C(OC(C)(C)C)=O)[N:3]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=3)[NH:4][N:3]=2)=[CH:24][CH:23]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 222608361-Boc-3-bromo-5-nitro-1H-indazole

생성물 1

HCID 534397423-(4-Fluorophenyl)-5-nitro-1H-indazole수율 100%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

The product from Step (b) (0.5 g, 1.5 mmol), 4-fluoro phenylboronic acid (0.31 g, 2.2 mmol) and Pd(dppf)2Cl2.CH2Cl2 (0.12 g, 0.15 mmol) were combined in 9 ml of 2:1 Dioxane/2 M K2CO3 The reaction mixture was sealed and heated to 95° C. for 18 h. The resulting biphasic mixture was cooled to room temperature. The phases were separated and the organic phase (top) was filtered. The aqueous layer was extracted once with EtOAc. The combined organic phases were washed with sat'd NaHCO3, water, brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (5% MeOH/CH2Cl2) to afford 0.37 g of the title compound, (100%); MS (ES+) m/e 259 [M+H]+.

후처리

  1. customwas sealed
  2. temperatureThe resulting biphasic mixture was cooled to room temperature
  3. customThe phases were separated
  4. filtrationthe organic phase (top) was filtered
  5. extractionThe aqueous layer was extracted once with EtOAc
  6. washThe combined organic phases were washed with sat'd NaHCO3, water, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography (5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-26ae3449e1e54625a1aa31e2d7e2bb03
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560467B2

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