Sodium borohydride → HCID 69185447, compound

HRID 2373222Notes

Reaction equation

HRID 2373222 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH3:21])[N:11]=[C:10]3[N:22]([CH2:25][CH3:26])[N:23]=[CH:24][C:9]=23)[CH:5]=[N:6][CH:7]=1.[BH4-].[Na+]>CO.O.O.O.O.O.O.O.[Ni](Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH3:21])[N:11]=[C:10]3[N:22]([CH2:25][CH3:26])[N:23]=[CH:24][C:9]=23)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 86602407HCID 86602407, compound

Product 1

HCID 69185447HCID 69185447, compoundYield 25.4%

Reagents, catalysts & solvents 3

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of ethyl (2E)-3-[4-(5-bromo-3-pyridyl)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl]acrylate (47 mg) in MeOH (2 ml) was added nickel chloride hexahydrate (7.26 mg) and sodium borohydride (10.7 mg) at −10° C. and the mixture was stirred at −10° C. for 15 minutes. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water and dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by preparative thin layer chromatography eluting with a mixture of EtOAc and n-hexane (1:1.5) to give ethyl 3-[4-(5-bromo-3-pyridyl)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (12 mg) as a light yellow oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography
  6. washeluting with a mixture of EtOAc and n-hexane (1:1.5)

Sources & evidence

ORD record
ord-b011a562759b47b7b73983cc49acf1dd
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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