Water → 4-Methyl-6-(methylsulfonyl)pyridin-3-amine

HRID 1811567

반응식

HRID 1811567 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.[CH3:10][S:11]([O-:13])=[O:12].[Na+].CNCCNC.O>[Cu].CS(C)=O>[CH3:10][S:11]([C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1)(=[O:13])=[O:12]

참가 물질

7

반응물 4

HCID 962WaterHCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 27344253-Amino-6-chloro-4-picoline

생성물 1

HCID 586715824-Methyl-6-(methylsulfonyl)pyridin-3-amine수율 27%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
150 °C

실험 절차

A mixture of 6-chloro-4-methyl-pyridin-3-ylamine (1.53 g, 11 mmol), sodium methanesulfinate (1.60 g, 16 mmol), copper catalyst (0.50 g, 0.99 mmol), and N1,N2-dimethylethane-1,2-diamine (0.214 mL, 2.0 mmol) in 20 mL DMSO was heated under microwave irradiation at 150° C. After 2 h, mixture was poured into ca. 200 mL water and extracted five times with ca. 200 mL AcOEt. Organic phases were dried over MgSO4, filtered, and concentrated. Residue was purified by column chromatography (AcOEt/hexane 5:1→AcOEt) to give 6-methanesulfonyl-4-methyl-pyridin-3-ylamine as a white solid (0.534 g, 27%). 1HNMR (DMSO-d6, 400 MHz) 32.4 (s, 3H), 3.08 (s, 3H), 6.08 (s, 2H), 7.59 (s, 1H), 7.97 (s, 1H). Exact mass calculated for C7H10N2O2S 186.05 found 187.0 (MH+).

후처리

  1. extractionextracted five times with ca. 200 mL AcOEt
  2. dry with materialOrganic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customResidue was purified by column chromatography (AcOEt/hexane 5:1→AcOEt)

출처 및 근거

ORD 기록
ord-b197c6bfbf21446cb32f5e377ae6ff9e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362248B2

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