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

HRID 1931567

反応式

HRID 1931567 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 2734754Benzene;bis(copper(1+));bis(trifluoromethanesulfonate)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fddbf3a95f2f487689d581f96cab69ff
出典データセット
uspto-grants-2012_05
特許番号
US08188098B2

関連ノート

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