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

HRID 1641479Notes

Reaction equation

HRID 1641479 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 66738757HCID 66738757, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4a0c9adb4c7b4abd901dabbf88a04f2d
Source dataset
uspto-grants-2012_02
Patent number
US08115014B2

Reaction notes

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