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Sodium hydride → 3-(1,2,3,4-Tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-1-methylpyrrolidin-2-one

HRID 517851
ノート
印刷プレビュー

反応式

HRID 517851 の反応式
[H-].[Na+].[CH3:3][N:4]1[CH2:17][CH2:16][C:7]2[NH:8][C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1.Br[CH:19]1[CH2:23][CH2:22][N:21]([CH3:24])[C:20]1=[O:25]>CN(C=O)C>[CH3:3][N:4]1[CH2:17][CH2:16][C:7]2[N:8]([CH:19]3[CH2:23][CH2:22][N:21]([CH3:24])[C:20]3=[O:25])[C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 111829543-Bromo-1-methylpyrrolidin-2-one

生成物 1

HCID 441601853-(1,2,3,4-Tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-1-methylpyrrolidin-2-one収率 13.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of NaH (36 mg, 1.5 mmol) and 2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (100 mg, 0.5 mmol) in DMF (5 mL) was stirred at 0° C. 3-bromo-1-methylpyrrolidin-2-one (176 mg, 1.0 mmol) in DMF (3 mL) was added dropwise to the reaction mixture which was stirred at RT for 12 hours. After completion of the reaction, the reaction mixture was quenched with ice cold water and the product extracted with Ethyl Acetate. The organic layer isolated was washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure and the crude obtained was purified by column chromatography to obtain 20 mg of 3-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-1-methylpyrrolidin-2-one. 1H NMR (CDCl3) FREEBASE 7.10 (s, 1H), 7.05 (d, 1H), 6.92 (d, 1H), 5.05 (m, 1H), 4.80 (m, 1H), 3.80 (m, 1H), 3.50 (m, 2H), 3.40 (m, 1H), 3.20 (m, 3H), 3.0 (s, 3H), 2.80 (s, 3H), 2.40 (s, 3H), 2.20 (m, 2H).

後処理

  1. stirringwas stirred at RT for 12 hours
  2. customAfter completion of the reaction
  3. customthe reaction mixture was quenched with ice cold water
  4. extractionthe product extracted with Ethyl Acetate
  5. customThe organic layer isolated
  6. washwas washed with water
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe crude obtained
  10. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-da830b056f0f47f696e672e760926316
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09115137B2

反応ノート

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