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 888420ノート

反応式

HRID 888420 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418851HCID 178418851、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-eac481ddd1c14ab4a72a7c0f24373771
出典データセット
uspto-grants-2012_08
特許番号
US08247401B2

反応ノート

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