Pyrazole → 3-Fluoro-2-(1H-pyrazol-1-YL)benzoic acid

HRID 2174992

반응식

HRID 2174992 반응식
[F:1][C:2]1[C:3](I)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[NH:12]1[CH:16]=[CH:15][CH:14]=[N:13]1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[Cs+].[Cs+]>O.[Cu]I.O1CCOCC1>[F:1][C:2]1[C:3]([N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

참가 물질

8

반응물 4

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 223203083-Fluoro-2-iodobenzoic acid

생성물 1

HCID 534097523-Fluoro-2-(1H-pyrazol-1-YL)benzoic acid수율 72.8%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

To a mixture of 3-fluoro-2-iodobenzoic acid (1.4 g, 5.26 mmol), 1H-pyrazole (0.72 g, 10.5 mmol), trans-N,N′-dimethyl-cyclohexane-1,2-diamine (0.17 mL, 1.05 mmol), CuI (50.1 mg, 0.26 mmol), dioxane (50 mL) and water (0.028 mL) was added Cs2CO3 (3.43 g, 10.5 mmol). The reaction mixture was heated to 100° C. for 1 h. The reaction mixture was cooled to ambient temperature then diluted with water. The aqueous layer was acidified to pH 2 and extracted with EtOAc (30 mL) three times. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1% HOAC/DCM) to the yield the title compound as a colorless oil (790 mg, 72%). 1H NMR (400 MHz, CDCl3): 7.85-7.73 (m, 1H), 7.54-7.44 (m, 1H), 7.44-7.34 (m, 1H), 6.55 (s, 1H).

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with EtOAc (30 mL) three times
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1% HOAC/DCM) to the

출처 및 근거

ORD 기록
ord-4a37681f5b8242f9a0c23fb910f94597
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062044B2

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