4-Fluoroiodobenzene → 1-(4-fluorophenyl)-6-methyl-1H-indazol-5-ol

HRID 563376

반응식

HRID 563376 반응식
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[OH:11].[C@@H]1(N)CCCC[C@H]1N.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:28][C:29]1[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=1>O1CCOCC1.CCOC(C)=O.[Cu]I>[F:28][C:29]1[CH:34]=[CH:33][C:32]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([OH:11])=[C:2]([CH3:1])[CH:10]=3)[CH:6]=[N:7]2)=[CH:31][CH:30]=1

참가 물질

8

반응물 4

HCID 96054-FluoroiodobenzeneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 229340186-methyl-1H-indazol-5-ol

생성물 1

HCID 592527721-(4-fluorophenyl)-6-methyl-1H-indazol-5-ol수율 38%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

6-Methyl-1H-indazol-5-ol (5.0 g, 33.7 mmol) was dissolved in 50 mL dry dioxane in a stainless steel pressure tube. Trans-1,2-cyclohexanediamine (2.0 mL, 17 mmol) was added followed by CuI (647 mg, 3.4 mmol) and then K3PO4 12.7 g, 60 mmol). After the addition of 4-fluoro-1-iodobenzene (3.9 mL, 33.7 mmol), the reactor was sealed and heated at 100 C for 24 h. The reactor was cooled and the contents were taken up in EtOAc, filtered through a SiO2 plug with EtOAc and concentrated in vacuo. The crude product was chromatographed on SiO2 using 1:3 EtOAc/hexanes to give 3.1 g (38% yield) of 1-(4-fluorophenyl)-6-methyl-1H-indazol-5-ol. MS found: (M+H)+=242.

후처리

  1. customthe reactor was sealed
  2. temperatureheated at 100 C for 24 h
  3. temperatureThe reactor was cooled
  4. filtrationfiltered through a SiO2 plug with EtOAc
  5. concentrationconcentrated in vacuo
  6. customThe crude product was chromatographed on SiO2 using 1:3 EtOAc/hexanes

출처 및 근거

ORD 기록
ord-76760e771f8a434eb7c889e7fa789c4b
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067447B2

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