7-Bromo-2-methylindole → HCID 66738757, 화합물

HRID 1641479노트

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HRID 1641479 반응식
C([Mg]Br)C.Br[CH2:6][C:7]1([CH2:10][C:11]#[N:12])[CH2:9][CH2:8]1.[Br:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[NH:21][C:20]([CH3:23])=[CH:19]2>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[NH:21][C:20]([CH3:23])=[C:19]2[CH2:6][C:7]1([CH2:10][C:11]#[N:12])[CH2:9][CH2:8]1

참가 물질

5

반응물 3

HCID 44130817-Bromo-2-methylindoleHCID 22637051[1-(Bromomethyl)cyclopropyl]acetonitrileHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 66738757HCID 66738757, 화합물수율 53.6%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

Ethyl magnesium bromide (3.0M diethyl ether solution, 72 mL) was slowly added dropwise under an argon atmosphere and ice-cooling to a solution of [1-(bromomethyl)cyclopropyl]acetonitrile (15 g) and 7-bromo-2-methyl-1H-indole (45 g) in toluene (250 mL), followed by stirring at 100° C. for 80 minutes. The reaction mixture was cooled to room temperature; quenched with a saturated aqueous ammonium chloride solution, diluted with water; and extracted with ethyl acetate. The organic layer was washed sequentially with water and brine. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by a purification system CombiFlash CompanionXL (manufactured by Isco, Co., Ltd., column: RediSep 350 g; hexane:ethyl acetate=95:5->70:30) to obtain title compound (14 g) having the following physical properties.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with a saturated aqueous ammonium chloride solution
  3. additiondiluted with water
  4. extractionand extracted with ethyl acetate
  5. washThe organic layer was washed sequentially with water and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by a purification system CombiFlash CompanionXL (manufactured by Isco, Co., Ltd., column: RediSep 350 g; hexane:ethyl acetate=95:5->70:30)

출처 및 근거

ORD 기록
ord-4a0c9adb4c7b4abd901dabbf88a04f2d
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08115014B2

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