Methanol → cyano-(2-cyano-9-oxo-9H-indeno[1,2-b]pyrazin-3-yl)-acetic acid tert-butyl ester

HRID 240315

反応式

HRID 240315 の反応式
[C:1]([CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2].[H-].[Na+].[O:13]=[C:14]1[C:26]2[C:21](=[N:22][C:23](C#N)=[C:24](C#N)[N:25]=2)[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=2.CO.[CH3:33][N:34](C=O)C>>[C:7]([O:6][C:4](=[O:5])[CH:3]([C:33]#[N:34])[C:1]1[N:2]=[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14](=[O:13])[C:26]2=[N:25][C:24]=1[C:23]#[N:22])([CH3:10])([CH3:9])[CH3:8]

参加物

6

反応物 5

HCID 887MethanolHCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 70693tert-Butyl cyanoacetateHCID 2929299-oxo-9H-indeno(1,2-b)pyrazine-2,3-dicarbonitrile

生成物 1

HCID 67059687cyano-(2-cyano-9-oxo-9H-indeno[1,2-b]pyrazin-3-yl)-acetic acid tert-butyl ester

実験手順

tert-Butyl cyanoacetate (292 mg, 2.07 mmol) was dissolved, under inert atmosphere, in dry DMF (4 ml) and NaH (60% dispersion in mineral oil, 90 mg, 2.24 mmol) was added portionwise. After 15 min, a solution of 1 (400 mg, 1.72 mmol) in dry DMF (3 ml) was added dropwise. After 16 h MeOH was added, the solvents were evaporated and the crude purified by flash chromatography (EtOAc:MeOH 9:1) affording cyano-(2-cyano-9-oxo-9H-indeno[1,2-b]pyrazin-3-yl)-acetic acid tert-butyl ester as dark red solid.

後処理

  1. customthe solvents were evaporated
  2. customthe crude purified by flash chromatography (EtOAc:MeOH 9:1)

出典と根拠

ORDレコード
ord-f5102584cb404712985212225415f4f6
出典データセット
uspto-grants-2014_02
特許番号
US08648076B2

関連ノート

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