Tetrahydrofuran → 5-[(2-Chloroethyl)pyrazol-1-ylmethyl]-6,7-dichloro-2,3-dimethoxyquinoxaline

HRID 1957113ノート

反応式

HRID 1957113 の反応式
[ClH:1].ClCC[C:5]1[CH:6]=[N:7][NH:8][CH:9]=1.[H-].[Na+].Br[CH2:13][C:14]1[C:23]([Cl:24])=[C:22]([Cl:25])[CH:21]=[C:20]2[C:15]=1[N:16]=[C:17]([O:28][CH3:29])[C:18]([O:26][CH3:27])=[N:19]2.O1[CH2:34][CH2:33]CC1>>[Cl:1][CH2:33][CH2:34][CH:13]([N:8]1[CH:9]=[CH:5][CH:6]=[N:7]1)[C:14]1[C:23]([Cl:24])=[C:22]([Cl:25])[CH:21]=[C:20]2[C:15]=1[N:16]=[C:17]([O:28][CH3:29])[C:18]([O:26][CH3:27])=[N:19]2

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 105459165-Bromomethyl-6,7-dichloro-2,3-dimethoxyquinoxalineHCID 190688934-(2-chloroethyl)-1H-pyrazole hydrochloride

生成物 1

HCID 543391965-[(2-Chloroethyl)pyrazol-1-ylmethyl]-6,7-dichloro-2,3-dimethoxyquinoxaline収率 63%

反応条件

温度
10 °C

実験手順

4-(2-Chloroethyl)pyrazole hydrochloride (250 mg, 1.0 mmol) was added to a suspension of sodium hydride (90 mg, 80% oil dispersion, 3.0 mmol) in dry tetrahydrofuran (10 mL) at 0° C. under nitrogen with stirring. Immediately 5-bromomethyl-6,7-dichloro-2,3-dimethoxyquinoxaline (352 mg, 1.0 mmol) was added, and the mixture was allowed to warm to 10° C. over 2 hours. The mixture was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic solution was dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography (gradient elution with ethyl acetate/hexane), followed by trituration with methanol gave 5-[(2-chloroethyl)pyrazol-1-ylmethyl]-6,7-dichloro-2,3-dimethoxyquinoxaline (254 mg, 63%), as a white solid.

後処理

  1. customThe mixture was partitioned between ethyl acetate (50 mL) and water (50 mL)
  2. dry with materialThe organic solution was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification
  5. washby flash chromatography (gradient elution with ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-200a6dfd31774c54a0d54b6b058b1f7f
出典データセット
uspto-grants-1998_07
特許番号
US05783572

反応ノート

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