Hydrochloric Acid → 3-(5-Cyano-3'-trifluoromethyl-[2,2']bipyridinyl-6-yl)-2-oxo-propionic acid ethyl ester

HRID 2113631ノート

反応式

HRID 2113631 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]#[N:19].[C:20](OCC)(=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].Cl>CCO.CC[O-].[Na+]>[CH2:24]([O:23][C:21](=[O:22])[C:20](=[O:26])[CH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]#[N:19])[CH3:25]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 586281916-Methyl-3'-trifluoromethyl-[2,2']bipyridinyl-5-carbonitrile

生成物 1

HCID 586282123-(5-Cyano-3'-trifluoromethyl-[2,2']bipyridinyl-6-yl)-2-oxo-propionic acid ethyl ester

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 2723922Sodium ethoxide溶媒

反応条件

温度
50 °C

実験手順

Dissolve 6-methyl-3′-trifluoromethyl-[2,2′]bipyridinyl-5-carbonitrile (150 mg, 0.570 mmol) and diethyl oxalate (150 mg, 1.03 mmol) in a solution of EtOH (2 mL) and 17% NaOEt in EtOH (0.6 mL, 1.71 mmol). Warm the mixture to 50° C. and stir overnight. Pour the mixture onto ice water (50 mL) and acidify with 3 N HCl. Extract with EtOAc (3×50 mL). Dry the combined organic extracts over Na2SO4 and remove the solvent under reduced pressure. Purify the crude product using silica gel chromatography eluting with EtOAc/hexane (1:1) to yield the title compound. MS 364.11 (M+1).

後処理

  1. additionPour the mixture onto ice water (50 mL)
  2. extractionExtract with EtOAc (3×50 mL)
  3. dry with materialDry the combined organic extracts over Na2SO4
  4. customremove the solvent under reduced pressure
  5. customPurify the crude product
  6. washeluting with EtOAc/hexane (1:1)

出典と根拠

ORDレコード
ord-33846280075b475f839875b92d3a4dfe
出典データセット
uspto-grants-2008_10
特許番号
US07432275B2

反応ノート

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