Bromine → HCID 89876355, compound

HRID 2169761Notes

Reaction equation

HRID 2169761 reaction equation
[Br:1]Br.[Cl:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]2[C:14](=[O:23])[N:15]([CH3:22])[N:16]=[C:17]([CH3:21])[C:18]=2[O:19][CH3:20])[CH:5]=1.C([O-])(O)=O.[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[CH3:20][O:19][C:18]1[C:17]([CH3:21])=[N:16][N:15]([CH3:22])[C:14](=[O:23])[C:13]=1[N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([Cl:3])=[C:5]1[Br:1]

Participants

6

Reactant 4

HCID 24408Bromine3×HCID 516892Sodium BicarbonateHCID 656671Sodium PyrosulfiteHCID 89876202HCID 89876202, compound

Product 1

HCID 89876355HCID 89876355, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Part of a solution of bromine (200 mg, 1.25 mmol) in DCM (4 mL) is added dropwise, slowly, to a solution of 4-(3-chloroindol-1-yl)-5-methoxy-2,6-dimethyl-pyridazin-3-one (184 mg, 0.606 mmol) in DCM (2 mL) at 0° C. The bromine decolourised as it was added and addition was continued cautiously until an orange colour just persisted. NaHCO3 (0.5 g saturated solution in water) is added cautiously, followed by sufficient sodium metabisulphite to decolorise the excess bromine. The resulting reaction mixture was extracted with DCM (3×60 mL) and the combined DCM layers were filtered through MgSO4 and concentrated in vacuo. The resulting yellow gum was purified by flash chromatography (combiflash, 0 to 30% DCM/EtOAc) to yield the desired pro duct 5-methoxy-2,6-dimethyl-4-(2-bromo-3-chloroindol-1-yl)pyridazin-3-one (115 mg, 0.301 mmol, 50% Yield) as a white solid.

Workup

  1. customat 0° C
  2. additionwas added
  3. additionaddition
  4. customThe resulting reaction mixture
  5. extractionwas extracted with DCM (3×60 mL)
  6. filtrationthe combined DCM layers were filtered through MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting yellow gum was purified by flash chromatography (combiflash, 0 to 30% DCM/EtOAc)

Sources & evidence

ORD record
ord-4c0d4f8ee43a4b099de4554d2b07aa0c
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

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