Methyl iodide → 4-allyl-5-(benzyloxy)-1-methyl-1H-indole

HRID 2235871ノート

反応式

HRID 2235871 の反応式
[CH2:1]([C:4]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)[CH:2]=[CH2:3].[H-].[Na+].[CH3:23]I>CN(C=O)C.O>[CH2:1]([C:4]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH3:23])[CH:2]=[CH2:3]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 593005385-(Benzyloxy)-4-(prop-2-en-1-yl)-1H-indole

生成物 1

HCID 593004174-allyl-5-(benzyloxy)-1-methyl-1H-indole収率 67%

試薬・触媒・溶媒 2

HCID 962Water触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

4-Allyl-5-(benzyloxy)-1H-indole (368.7 mg, 1.40 mmol) (Example 58) was dissolved in anhydrous DMF (12 mL) under an inert atmosphere, and the reaction mixture was cooled in an ice-water bath. Sodium hydride (60% in mineral oil) (181 mg, 1.68 mmol) was added, and the reaction mixture was stirred for an additional 30 min. Methyl iodide (278 mg, 1.96 mmol) was added and stirring at rt was continued for 30 min. The reaction mixture was heated to 40° C. for 12 h, cooled to rt, and water (10 drops) was added. The reaction mixture was concentrated under reduced pressure, after which water was added, and the aqueous phase was extracted with EtOAc (2×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:15) gave 259 mg (67%) of the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 3.72 (m, 5H), 4.98 (d, 1H), 5.07 (d, 1H), 5.12 (s, 2H), 6.06 (m, 1H), 6.47 (s, 1H), 7.00 (d, 1H), 7.03 (s, 1H), 7.12 (d, 1H), 7.31 (m, 1H), 7.39 (m, 2H), 7.48 (m, 2H).

後処理

  1. temperaturethe reaction mixture was cooled in an ice-water bath
  2. stirringstirring at rt
  3. waitwas continued for 30 min
  4. temperaturecooled to rt
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additionafter which water was added
  7. extractionthe aqueous phase was extracted with EtOAc (2×)
  8. dry with materialThe combined organic phases were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customPurification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:15)

出典と根拠

ORDレコード
ord-0b943c57c7f84bd2a4cde95cb5414a5c
出典データセット
uspto-grants-2010_05
特許番号
US07714004B2

反応ノート

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