N-bromobutanimide → 3-Bromo-5-methylpyrrolo[1,2-b]cinnolin-10(5H)-one

HRID 1639258Notes

Reaction equation

HRID 1639258 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][N:10]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13](=[O:20])[C:12]2=[CH:21][CH:22]=[CH:23][N:11]12>C1COCC1>[Br:1][C:23]1[N:11]2[N:10]([CH3:9])[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13](=[O:20])[C:12]2=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 141715685-methylpyrrolo[1,2-b]cinnolin-10(5H)-one

Product 1

HCID 141715733-Bromo-5-methylpyrrolo[1,2-b]cinnolin-10(5H)-oneYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-bromosuccinimide (3.5 g) in 50 mL of THF was added dropwise to a solution of 5-methylpyrrolo[1,2-b]cinnolin-10(5H)-one (3.8 g) in 70 mL of dry THF at 0° C. After 16 hours of stirring at room temperature, the solution was concentrated and the residue taken up in 200 mL of CHCl3. This solution was washed with H2O, dried over MgSO4, filtered and concentrated. The residue was purified by HPLC (silica, dichloromethane) to give 3.8 g of yellow crystals. This material was recrystallized from ether to give 3.6 g of pale yellow crystals, mp 103°-105° C.

Workup

  1. concentrationthe solution was concentrated
  2. washThis solution was washed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by HPLC (silica, dichloromethane)

Sources & evidence

ORD record
ord-e41c997be5114ad9a29b5de0e37d5199
Source dataset
uspto-grants-1989_11
Patent number
US04883794

Reaction notes

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