Sodium borohydride → HCID 59176789, compound

HRID 215967Notes

Reaction equation

HRID 215967 reaction equation
[BH4-].[Na+].[C:3]1([CH:13]=[C:14]2[N:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]3=[N:16][C:15]2=[O:23])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1>C(O)C.CO>[C:3]1([CH2:13][CH:14]2[N:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]3=[N:16][C:15]2=[O:23])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 686995473-[1-Naphthalen-1-yl-methylidene]-imidazo[1,2-a]pyridin-2-one

Product 1

HCID 59176789HCID 59176789, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 137 mg (3.7 mmol) of sodium borohydride in 15 mL of ethanol is added a solution of 500 mg (1.8 mmol) of 3-[1-naphthalen-1-yl-methylidene]-imidazo[1,2-a]pyridin-2-one in 50 mL of methanol, dropwise at −78° C. After stirring for 10 min at −78° C., the reaction mixture is quenched with saturated aqueous ammonium chloride solution at −78° C. The product is extracted with dichloromethane. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired compound.

Workup

  1. customdropwise at −78° C
  2. customthe reaction mixture is quenched with saturated aqueous ammonium chloride solution at −78° C
  3. extractionThe product is extracted with dichloromethane
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22fb3b9ad2bc48f99a18ffab9dce5bc0
Source dataset
uspto-grants-2012_06
Patent number
US08193214B2

Reaction notes

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