N-bromobutanimide → methyl 2-(2-bromo-1-methyl-1H-indol-3-yl)pentanoate

HRID 590999Notes

Reaction equation

HRID 590999 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]([CH2:16][CH2:17][CH3:18])[C:12]([O:14][CH3:15])=[O:13])=[CH:3]1.[Br:19]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[Br:19][C:3]1[N:2]([CH3:1])[C:10]2[C:5]([C:4]=1[CH:11]([CH2:16][CH2:17][CH3:18])[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 70817995methyl 2-(1-methyl-1H-indol-3-yl)pentanoate

Product 1

HCID 70819053methyl 2-(2-bromo-1-methyl-1H-indol-3-yl)pentanoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 2-(1-methyl-1H-indol-3-yl)pentanoate (12b) (860 mg, 3.44 mmol) and N-bromosuccinimide (623 mg, 3.5 mmol) in tetrachloromethane (20 mL) was stirred at room temperature for 5 hours. The mixture was then filtered and the filtrate was washed with water (10 mL), brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure to afford the desired product (12c) as a brown oil without further purification (1.13 g, 3.44 mmol, 100%).

Workup

  1. filtrationThe mixture was then filtered
  2. washthe filtrate was washed with water (10 mL), brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b1dfad4959c743908bde6e7ed3469dce
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

Loading…