Dimethylformamide → methyl 2-(5-bromo-3-cyano-2-oxopyridin-1(2H)-yl)acetate

HRID 869906노트

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HRID 869906 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:9]#[N:10])[C:5](=[O:8])[NH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]([O:21][CH3:22])=[O:20].CN(C=O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]#[N:10])[C:5](=[O:8])[N:6]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:7]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 72048705-Bromo-2-hydroxypyridine-3-carbonitrile

생성물 1

HCID 117640756methyl 2-(5-bromo-3-cyano-2-oxopyridin-1(2H)-yl)acetate수율 74.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
80 °C

실험 절차

To 5-bromo-3-cyano-2(1H)-pyridinone (1.4 g, 7.0 mmol) and potassium carbonate (1.9 g, 1.3 mL, 14.1 mmol), THF (26.4 mL) and methyl chloroacetate (1.53 g, 1.2 mL, 14.1 mmol) were added. The reaction was stirred at 80° C. The starting material didn't dissolve well in THF. After 3.5 hours, mainly staring material was observed. DMF (18 mL) was added and the starting material went into solution. The reaction was heated at 80° C. for 45 minutes. The desired mass was observed by LCMS. The reaction was filtered using ethyl acetate and the solvent was evaporated under reduced pressure. The crude product was separated by column chromatography on silica gel (0-100% ethyl acetate in hexane) to yield methyl 2-(5-bromo-3-cyano-2-oxopyridin-1(2H)-yl)acetate as a yellow solid (1.42 g, 74%). ESI-MS m/z calc. 271.07. found 271.3 (M+1)+. Retention time 0.59 minutes.

후처리

  1. temperatureThe reaction was heated at 80° C. for 45 minutes
  2. filtrationThe reaction was filtered
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude product was separated by column chromatography on silica gel (0-100% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-a44819bb1a8c4d589dc52742d885c810
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969386B2

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