Bromine → HCID 67215796, compound

HRID 1677572Notes

Reaction equation

HRID 1677572 reaction equation
C([O-])(=O)C.[Na+].[CH:6]1[N:7]=[C:8]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH3:27])[CH:18]=2)=[O:16])[N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12.[Br:28]Br.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:28][C:6]1[N:7]=[C:8]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH3:27])[CH:18]=2)=[O:16])[N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12

Participants

6

Reactant 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 67215265HCID 67215265, compound

Product 1

HCID 67215796HCID 67215796, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

3.51 g (0.043 mol) of sodium acetate are added to 9.8 g (0.033 mol) of (imidazo[1,5-a]pyridin-3-yl)(3-methoxy-4-nitrophenyl)methanone obtained in example 1 in 170 ml of chloroform, followed, dropwise, by a solution of 1.85 ml (0.036 mol) of bromine in 15 ml of chloroform, the medium being maintained at ambient temperature. On completion of the introduction, the mixture is stirred for a further 1 hour at the same temperature. The reaction medium is poured onto a saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic phase is separated by settling, washed with an aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue is taken up in a toluene/dichloromethane mixture and then purified by filtration through a bed of silica gel, elution being carried out with toluene. After evaporation, 7.71 g of a yellow solid are collected. Melting point: 189° C.; 1H NMR (CDCl3): 4.10 (3H, s), 7.23-7.29 (1H, m), 7.41-7.46 (1H, m), 7.78 (1H, d), 7.96 (1H, d), 8.14-8.20 (2H, m), 9.90 (1H, d)

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic phase is separated
  3. washwashed with an aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationpurified by filtration through a bed of silica gel, elution
  7. customAfter evaporation, 7.71 g of a yellow solid
  8. customare collected

Sources & evidence

ORD record
ord-2e0662c735da48be988edd1d5c5f0af8
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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