Sodium borohydride → HCID 89876292, compound

HRID 2169772Notes

Reaction equation

HRID 2169772 reaction equation
[C:1]([C:4]1[C:5]([O:23][CH3:24])=[C:6]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([Cl:21])=[C:13]2[Cl:22])[C:7](=[O:11])[N:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[Cl:22][C:13]1[N:12]([C:6]2[C:7](=[O:11])[N:8]([CH3:10])[N:9]=[C:4]([CH:1]([OH:3])[CH3:2])[C:5]=2[O:23][CH3:24])[C:20]2[C:15]([C:14]=1[Cl:21])=[CH:16][CH:17]=[CH:18][CH:19]=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 89876303HCID 89876303, compound

Product 1

HCID 89876292HCID 89876292, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 6-acetyl-4-(2,3-dichloroindol-1-yl)-5-methoxy-2-methyl-pyridazin-3-one (500 mg, 1.37 mmol) in ethanol (1 mL) at 0° C. is added sodium borohydride (79 mg, 2.05 mmol). After stirring for 20 min, the reaction is quenched with water (10 mL), then concentrated under reduced pressure to remove most of the ethanol. The aqueous solution is then extracted with Et2O (20 mL×2), then concentrated under reduced pressure to give the desired product 4-(2,3-dichloroindol-1-yl)-6-(1-hydroxyethyl)-5-methoxy-2-methyl-pyridazin-3-one (379 mg, 1.03 mmol, 75%) as a white solid.

Workup

  1. customthe reaction is quenched with water (10 mL)
  2. concentrationconcentrated under reduced pressure
  3. customto remove most of the ethanol
  4. extractionThe aqueous solution is then extracted with Et2O (20 mL×2)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4bdf3cb1509349539fb7f9fe5c0e1d02
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

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