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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
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HRID 517851 반응식
[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
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참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-da830b056f0f47f696e672e760926316
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115137B2

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