Tert-butyl 3-(1-amino-2,2,2-trifluoroethyl)-5-bromobenzoate → Tert-butyl 3-(1-amino-2,2,2-trifluoroethyl)-5-(5-methylpyridin-2-yl)benzoate

HRID 888420노트

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HRID 888420 반응식
[NH2:1][CH:2]([C:7]1[CH:8]=[C:9]([CH:17]=[C:18](Br)[CH:19]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:3]([F:6])([F:5])[F:4].Br[Zn][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][N:24]=1>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[NH2:1][CH:2]([C:7]1[CH:8]=[C:9]([CH:17]=[C:18]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][N:24]=2)[CH:19]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:3]([F:6])([F:5])[F:4]

참가 물질

5

반응물 2

HCID 59539695Tert-butyl 3-(1-amino-2,2,2-trifluoroethyl)-5-bromobenzoateHCID 178427803HCID 178427803, 화합물

생성물 1

HCID 68496539Tert-butyl 3-(1-amino-2,2,2-trifluoroethyl)-5-(5-methylpyridin-2-yl)benzoate수율 96%

시약·촉매·용매 2

HCID 178418851HCID 178418851, 화합물촉매HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

To a solution of tert-butyl 3-(1-amino-2,2,2-trifluoroethyl)-5-bromobenzoate (1.4 g, 3.95 mmol) in dioxane (20 mL) was added bis(tri-t-butylphosphine)palladium(0) (0.06 g, 0.12 mmol). The mixture was degassed with nitrogen and bromo(5-methylpyridin-2-yl)zinc (0.5 M in THF; 23.7 mL, 11.9 mmol) was added. The mixture was heated to 70° C. After 1 h, the mixture was cooled to ambient temperature and filtered with Celite. The filtrate was concentrated to remove dioxane and saturated NaHCO3 was added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→60% dichloromethane/ethyl acetate) gave the title compound (1.39 g). MS 367.1 (M+1).

후처리

  1. additionwas added
  2. temperaturethe mixture was cooled to ambient temperature
  3. filtrationfiltered with Celite
  4. concentrationThe filtrate was concentrated
  5. customto remove dioxane and saturated NaHCO3
  6. additionwas added
  7. extractionThe mixture was extracted with ethyl acetate (3×)
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification by silica gel chromatography (100% dichloromethane→60% dichloromethane/ethyl acetate)

출처 및 근거

ORD 기록
ord-eac481ddd1c14ab4a72a7c0f24373771
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247401B2

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