Ammonia → N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine

HRID 1750053노트

반응식

HRID 1750053 반응식
Br[C:2]1[C:3]([NH:13][CH3:14])=[N:4][CH:5]=[C:6]([S:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1.C(CC(=O)C)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[NH3:28]>[Cu+2].C(CC(=O)C)(=O)C.O.CN1C(=O)CCC1>[CH3:14][NH:13][C:3]1[C:2]([NH2:28])=[CH:7][C:6]([S:8][C:9]([F:12])([F:11])[F:10])=[CH:5][N:4]=1

참가 물질

8

반응물 4

HCID 222AmmoniaHCID 10796Cesium carbonateHCID 31261AcetylacetoneHCID 67981267(3-Bromo-5-trifluoromethylsulfanylpyridine-2-yl)-methylamine

생성물 1

HCID 68091243N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine

시약·촉매·용매 3

HCID 21863952acetylacetone copper(II)촉매HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
110 °C

실험 절차

1.96 g of (3-bromo-5-trifluoromethylsulfanylpyridin-2-yl)-methylamine, 89 mg of acetylacetone copper(II), 0.27 g of acetylacetone, 2.34 g of cesium carbonate, 7 ml of NMP and 5 ml of aqueous ammonia (28%) were charged to a pressure-resistant reactor and stirred at 110° C. for 8.5 hours. Water was added to the reaction mixture cooled to room temperature, and the insoluble matter was filtered with celite (registered trademark), and then the filtered matter was washed with ethyl acetate, and the filtrate was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 1.18 g of N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine.

후처리

  1. temperaturecooled to room temperature
  2. filtrationthe insoluble matter was filtered with celite (registered trademark)
  3. washthe filtered matter was washed with ethyl acetate
  4. extractionthe filtrate was extracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0348384267e94c4f870e3c1b538a9756
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156838B2

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