Water → Methyl 2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoate

HRID 535445Notes

Reaction equation

HRID 535445 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[N:30]3[C:25]([CH:26]=[CH:27][CH:28]=[CH:29]3)=[CH:24][C:23]=2[CH3:31])=[O:21])=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].O>ClCCl>[NH2:9][C:10]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[N:30]3[C:25]([CH:26]=[CH:27][CH:28]=[CH:29]3)=[C:24]([Br:1])[C:23]=2[CH3:31])=[O:21])=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 66653318Methyl 2-amino-5-[(2-methylindolizin-3-yl)carbonyl]benzoate

Product 1

HCID 57500395Methyl 2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoateYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.492 g (2.73 mmol) of N-bromosuccinimide is added, under an inert atmosphere at ambient temperature, to 0.812 g (2.6 mmol) of methyl 2-amino-5-[(2-methylindolizin-3-yl)carbonyl]benzoate in 17 ml of dichloromethane. The reaction medium is stirred for 2 hours and then hydrolysed with water. The aqueous phase is extracted with dichloromethane. The organic phase obtained is washed with a saturated aqueous solution of sodium hydrogen carbonate and then with a saturated aqueous solution of sodium chloride, dried over sodium sulphate, filtered, and then concentrated under reduced pressure. The solid obtained is purified by silica gel column chromatography, elution being carried out with dichloromethane. 0.9 g of a yellow solid is obtained.

Workup

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. customThe organic phase obtained
  3. washis washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialwith a saturated aqueous solution of sodium chloride, dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe solid obtained
  8. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-617710fefd244c6594e2ffee7207c28f
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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