Water → 2,8-dimethyl-5-((2-phenyl-1,3-dioxolan-2-yl)methyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 400698ノート

反応式

HRID 400698 の反応式
[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[H-].[Na+].Br[CH2:19][C:20]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:24][CH2:23][CH2:22][O:21]1.O>CN(C=O)C>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6]([CH2:19][C:20]3([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[O:21][CH2:22][CH2:23][O:24]3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 2915742-(Bromomethyl)-2-phenyl-1,3-dioxolane

生成物 1

HCID 509437282,8-dimethyl-5-((2-phenyl-1,3-dioxolan-2-yl)methyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2 g, 10 mmol) was dissolved in 20 mL of DMF. The resulting solution was cooled in an ice-water bath and sodium hydride (840 mg, 4.2 mmol) was added under nitrogen atmosphere. 2-Bromomethyl-2-phenyl[1,3]dioxolane (2.43 g, 10 mmol) was added and the reaction mixture was heated at 100° C. overnight. Water was added and the product was extracted with EtOAc. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-5% MeOH:DCM.

後処理

  1. temperatureThe resulting solution was cooled in an ice-water bath
  2. extractionthe product was extracted with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 0-5% MeOH

出典と根拠

ORDレコード
ord-75f0a078be004938a91ce3ab15c4947a
出典データセット
uspto-grants-2014_06
特許番号
US08741919B2

反応ノート

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