Iodine → HCID 89876160, compound

HRID 2169768Notes

Reaction equation

HRID 2169768 reaction equation
[Cl:1][C:2]1[N:3]([C:12]2[C:17](=[O:18])[N:16]([CH3:19])[N:15]=[C:14]([CH:20]=O)[C:13]=2[O:22][CH3:23])[C:4]2[C:9]([C:10]=1[Cl:11])=[CH:8][CH:7]=[CH:6][CH:5]=2.[OH-].[NH4+:25].II>C1COCC1>[Cl:1][C:2]1[N:3]([C:12]2[C:17](=[O:18])[N:16]([CH3:19])[N:15]=[C:14]([C:20]#[N:25])[C:13]=2[O:22][CH3:23])[C:4]2[C:9]([C:10]=1[Cl:11])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 89876173HCID 89876173, compound

Product 1

HCID 89876160HCID 89876160, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-(2,3-dichloroindol-1-yl)-4-methoxy-1-methyl-6-oxo-pyridazine-3-carbaldehyde (98 mg, 0.278 mmol) in THF (1.5 mL) is added ammonium hydroxide (30% aq. solution, 1.5 mL), followed by iodine (92 mg, 0.362 mmol), which caused a dark brown colour to appear. The resulting reaction mixture was stirred for 1 h and then quenched with NaHCO3 solution (5 mL) and Na2S2O3 solution (5 mL). This caused the reaction to change from dark brown to a clear pale yellow mixture. After stirring for 10 min the reaction was extracted with DCM (20 mL×2), dried (MgSO4) and concentrated under reduced pressure to afford the desired pro duct 5-(2,3-dichloroindol-1-yl)-4-methoxy-1-methyl-6-oxo-pyridazine-3-carbonitrile (82 mg, 0.235 mmol, 85%) as a yellow foam that crushed into a yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. customquenched with NaHCO3 solution (5 mL) and Na2S2O3 solution (5 mL)
  3. customthe reaction
  4. stirringAfter stirring for 10 min the reaction
  5. extractionwas extracted with DCM (20 mL×2)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-28fe9aa1a02148ee92e4f0cef978a144
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

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