Sodium borohydride → Benzyl-(2-phenyl-2H-indazol-3-yl)-amine

HRID 1690515Notes

Reaction equation

HRID 1690515 reaction equation
[BH4-].[Na+].[C:3]1([N:9]2[C:17]([N:18]=[CH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:16]3[C:11]([CH:12]=[CH:13][CH:14]=[CH:15]3)=[N:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C>[CH2:19]([NH:18][C:17]1[N:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:10]=[C:11]2[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]2)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66905500HCID 66905500, compound

Product 1

HCID 45110618Benzyl-(2-phenyl-2H-indazol-3-yl)-amineYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (245 mg, 6.46 mmol) was added to a suspension of (2-phenyl-2H-indazol-3-yl)-[1-phenyl-methylidene]-amine (480 mg, 1.61 mmol) in ethanol (13 ml) at ambient temperature under an argon atmosphere. The reaction mixture was stirred at ambient temperature for 12 h, poured onto ice water/aqueous NaHCO3 solution 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure, the resulting yellow oil was purified by column chromatography (silica gel, iPrOAc/heptane) to give the title compound (314 mg, 1.05 mmol; 65%) as yellow oil. MS: m/e=300.4 [M+H+].

Workup

  1. additionpoured onto ice water/aqueous NaHCO3 solution 1/1
  2. extractionextracted two times with iPrOAc
  3. washThe combined extracts were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure
  7. customthe resulting yellow oil was purified by column chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-d7550530fd714917983e55437bd6b25c
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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