Dichloromethane → HCID 89876177, compound

HRID 2169762Notes

Reaction equation

HRID 2169762 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[C:12](=[O:21])[N:13]([CH3:20])[N:14]=[C:15]([CH3:19])[C:16]=2[O:17][CH3:18])[CH:3]=1.C([O-])(O)=O.[Na+].C(Cl)[Cl:28]>>[CH3:18][O:17][C:16]1[C:15]([CH3:19])=[N:14][N:13]([CH3:20])[C:12](=[O:21])[C:11]=1[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([Br:1])=[C:3]1[Cl:28]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 516892Sodium BicarbonateHCID 89876102HCID 89876102, compound

Product 1

HCID 89876177HCID 89876177, compoundYield 87%

Procedure

A solution of SO2Cl2 (47 μl, 0.583 mmol) in DCM (2 mL) is added dropwise to a solution of 4-(3-bromoindol-1-yl)-5-methoxy-2,6-dimethyl-pyridazin-3-one (203 mg, 0.583 mmol) in DCM (6 mL) at 0° C. The solution went pale yellow. After stirring for 5 min the cooling bath is removed and the resulting reaction mixture stirred at ambient temperature for 2 h. The reaction mixture is shaken well with a solution of NaHCO3. The layers are separated and the aqueous layer extracted with DCM (3×20 mL). The combined DCM layers were filtered through MgSO4 and concentrated in vacuo. The resulting solid was purified by flash chromatography (combiflash, 0 to 10% DCM/EtOAc) to yield the desired product 5-methoxy-2,6-dimethyl-4-(2-chloro-3-bromoindol-1-yl)pyridazin-3-one (194 mg, 0.507 mmol, 87% Yield).

Workup

  1. customis removed
  2. customthe resulting reaction mixture
  3. stirringstirred at ambient temperature for 2 h
  4. customThe layers are separated
  5. extractionthe aqueous layer extracted with DCM (3×20 mL)
  6. filtrationThe combined DCM layers were filtered through MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was purified by flash chromatography (combiflash, 0 to 10% DCM/EtOAc)

Sources & evidence

ORD record
ord-42b3d8f4f1e24347a0081a717fb6949e
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

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