Sodium Nitrite → 5-cyclopropyl-1H-pyrazolo[3,4-c]pyridine

HRID 1527300Notes

Reaction equation

HRID 1527300 reaction equation
[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([NH2:10])=[C:6]([CH3:11])[CH:5]=2)[CH2:3][CH2:2]1.[N:12]([O-])=O.[Na+]>CC(O)=O.O>[CH:1]1([C:4]2[CH:5]=[C:6]3[CH:11]=[N:12][NH:10][C:7]3=[CH:8][N:9]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 682833106-Cyclopropyl-4-methylpyridin-3-amine

Product 1

HCID 682844125-cyclopropyl-1H-pyrazolo[3,4-c]pyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 6-cyclopropyl-4-methylpyridin-3-amine (130 mg, 0.88 mmol) in AcOH (10 mL) was treated with a solution of sodium nitrite (61 mg, 0.88 mmol) in water (0.5 mL). The reaction mixture was stirred at RT for 15 min and then was allowed to stand at RT for 24 h. AcOH was evaporated under reduced pressure and the residual aqueous solution was partitioned between EtOAc and sat. aq. NaHCO3. The organic solution was washed with water and brine, then dried (Phase separator) and concentrated under. MS (LC-MS): 160 [M+H]+, tR (HPLC conditions c): 2.07 min.

Workup

  1. waitto stand at RT for 24 h
  2. customAcOH was evaporated under reduced pressure
  3. customthe residual aqueous solution was partitioned between EtOAc and sat. aq. NaHCO3
  4. washThe organic solution was washed with water and brine
  5. customdried (Phase separator)
  6. concentrationconcentrated under
  7. custom2.07 min.

Sources & evidence

ORD record
ord-e9adfbd507fd4e1bba64e046ae86d72b
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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