Sodium nitromalonaldehyde hydrate → HCID 178526793, compound

HRID 1943921Notes

Reaction equation

HRID 1943921 reaction equation
[F:1][C:2]([F:11])([F:10])[CH2:3][C:4]1[CH:8]=[C:7]([NH2:9])[NH:6][N:5]=1.O.[N+:13]([CH:16]([CH:19]=O)[CH:17]=O)([O-:15])=[O:14].[Na]>O>[N+:13]([C:16]1[CH:17]=[C:8]2[C:4]([CH2:3][C:2]([F:1])([F:10])[F:11])=[N:5][NH:6][C:7]2=[N:9][CH:19]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 71317419Sodium nitromalonaldehyde hydrateHCID 178507583HCID 178507583, compound

Product 1

HCID 178526793HCID 178526793, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

A round-bottom flask was charged with 3-(2,2,2-trifluoroethyl)-1H-pyrazol-5-amine (0.145 g, 0.878 mmol, WO 2008/005956), sodium nitromalonaldehyde monohydrate (0.150 g, 0.966 mmol) and water (3.5 mL). The reaction mixture was heated at 85° C. for 16 hours. The reaction mixture was poured into water and subsequently extracted with ethyl acetate (2×). The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography to afford 5-nitro-3-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-b]pyridine (0.078 g, 36%).

Workup

  1. extractionsubsequently extracted with ethyl acetate (2×)
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-c0539f7e64b646f5ba36ae7c7ce12659
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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