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

HRID 869906

反応式

HRID 869906 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a44819bb1a8c4d589dc52742d885c810
出典データセット
uspto-grants-2015_03
特許番号
US08969386B2

関連ノート

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