2-Bromopropane → HCID 68184277, compound

HRID 2199969Notes

Reaction equation

HRID 2199969 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[Cl-].[Al+3].[Cl-].[Cl-].Br[CH:19]([CH3:21])[CH3:20].C(=O)([O-])O.[Na+]>ClCCl>[CH:19]([C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=2)[NH:1][CH:2]=1)([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 516892Sodium BicarbonateHCID 639844Methyl indole-6-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 68184277HCID 68184277, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl indole-6-carboxylate (497 mg) in dichloromethane (15 mL) were added aluminum chloride (831 mg) and 2-bromopropane (0.27 mL) at room temperature, and then the reaction mixture was stirred at room temperature for 1 hour. To the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (65 mg) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-25c0f6bb0b794a41b90e6c474064ad33
Source dataset
uspto-grants-2016_06
Patent number
US09359350B2

Reaction notes

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