Water → 2-Methyl-6-(methylsulfonyl)pyridin-3-amine

HRID 1931567

반응식

HRID 1931567 반응식
[NH2:1][C:2]1[C:3]([CH3:9])=[N:4][C:5](Br)=[CH:6][CH:7]=1.[CH3:10][S:11]([O-:13])=[O:12].[Na+].CNCCNC.O>CS(C)=O.C1C=CC=CC=1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+].[Cu+].C(OCC)(=O)C>[CH3:10][S:11]([C:5]1[N:4]=[C:3]([CH3:9])[C:2]([NH2:1])=[CH:7][CH:6]=1)(=[O:13])=[O:12]

참가 물질

8

반응물 4

HCID 962WaterHCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 144180456-Bromo-2-methylpyridin-3-amine

생성물 1

HCID 510505272-Methyl-6-(methylsulfonyl)pyridin-3-amine수율 50.2%

시약·촉매·용매 3

HCID 2734754Benzene;bis(copper(1+));bis(trifluoromethanesulfonate)촉매HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
150 °C

실험 절차

A mixture of 3-amino-6-bromo-2-methylpyridine (ECA International Corporation, Palatine, Ill., USA; 2.0 g, 10.7 mmol), sodium methanesulfinate (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 5.13 g, 42.8 mmol), copper trifluoromethanesulfonate benzene complex (598 mg, 1.07 mmol), and N,N′-dimethylethylenediamine (115 μL, 1.07 mmol) in dimethylsulfoxide (15 mL) was heated at 150° C. for 4 h. The mixture was cooled and water and ethyl acetate were added. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed twice with water, and then concentrated to approximately 5 mL. This gave a precipitate which was filtered off, washed with a small amount of ethyl acetate and air dried to give 6-Methanesulfonyl-2-methyl-pyridin-3-ylamine (1 g, 50%) as a brown powder. 1H NMR (300 MHz, DMSO-d6) δ 2.30 (s, 3H), 3.05 (s, 3H), 6.04 (br s, 2H), 6.98 (d, 1H, J=8.4 Hz), 7.55 (d, 1H, J=8.2 Hz).

후처리

  1. temperatureThe mixture was cooled
  2. extractionThe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed twice with water
  4. concentrationconcentrated to approximately 5 mL
  5. customThis gave a precipitate which
  6. filtrationwas filtered off
  7. washwashed with a small amount of ethyl acetate and air
  8. customdried

출처 및 근거

ORD 기록
ord-fddbf3a95f2f487689d581f96cab69ff
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188098B2

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