Sodium Nitrite → 5-(Trifluoromethyl)-1H-pyrazolo[3,4-C]pyridine

HRID 1527304Notes

Reaction equation

HRID 1527304 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][C:3]=1[NH2:12].[N:13]([O-])=O.[Na+]>C(O)(=O)C.O>[F:10][C:8]([F:11])([F:9])[C:6]1[CH:7]=[C:2]2[CH:1]=[N:13][NH:12][C:3]2=[CH:4][N:5]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 497579514-Methyl-6-(trifluoromethyl)pyridin-3-amine

Product 1

HCID 682833945-(Trifluoromethyl)-1H-pyrazolo[3,4-C]pyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 4-methyl-6-(trifluoromethyl)pyridin-3-amine [944317-54-8] (1.00 g, 5.68 mmol) in acetic acid (75 mL) was treated with a solution of sodium nitrite (392 mg, 5.68 mmol) in water (1 mL). The reaction mixture was stirred at RT for 15 min and then was allowed to stand at ambient temperature for 48 h. Acetic acid 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 vacuum. MS (LC-MS): 188 [M+H]+, tR (HPLC conditions k): 2.49 min.

Workup

  1. waitto stand at ambient temperature for 48 h
  2. customAcetic acid 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 vacuum
  7. custom2.49 min.

Sources & evidence

ORD record
ord-3523a765bb9d4d61ad5ae53a73f00d9f
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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