Methyl iodide → N-((5-Bromopyridin-3-yl)methyl)-N-methylethanesulfonamide

HRID 1623508노트

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HRID 1623508 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].I[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]([CH3:18])[S:10]([CH2:13][CH3:14])(=[O:11])=[O:12])[CH:5]=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58215658N-((5-bromopyridin-3-yl)methyl)ethanesulfonamide

생성물 1

HCID 66788309N-((5-Bromopyridin-3-yl)methyl)-N-methylethanesulfonamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
-10 °C

실험 절차

To a solution of ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide (0.21 g, 0.752 mmol), prepared as described in Example 11a, in DMF (6 mL) at −10° C., was added sodium hydride (60% oil dispersion, 39 mg, 0.98 mmol). The reaction was stirred for 15 minutes at which time iodomethane (0.056 ml, 0.903 mmol) dissolved in DMF (1 mL) was added. The reaction was stirred at −10° C. for an additional 15 minutes and was then quenched with ammonia hydroxide (2 mL). The reaction was diluted with brine and extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate, 0 to 80%) to provide ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-methyl-amide; MS: (ES+) m/z 293.1 (M+H)+.

후처리

  1. additionwas added
  2. customwas then quenched with ammonia hydroxide (2 mL)
  3. additionThe reaction was diluted with brine
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate, 0 to 80%)

출처 및 근거

ORD 기록
ord-2d4081b673b441b7af240259066e3c9e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778972B2

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