2-(2-Methyl-1,3-dioxolan-2-yl)acetaldehyde → 3-bromo-4-(5-methyl-1H-pyrazol-1-yl)-5-nitropyridine

HRID 524920Notes

Reaction equation

HRID 524920 reaction equation
[CH3:1][C:2]1([CH2:7][CH:8]=O)OCCO1.[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[C:16]=1[NH:17][NH2:18]>C(O)C>[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[C:16]=1[N:17]1[C:2]([CH3:1])=[CH:7][CH:8]=[N:18]1

Participants

4

Reactant 2

HCID 110079262-(2-Methyl-1,3-dioxolan-2-yl)acetaldehydeHCID 867209743-Bromo-4-hydrazinyl-5-nitropyridine

Product 1

HCID 867209753-bromo-4-(5-methyl-1H-pyrazol-1-yl)-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-methyl-1,3-dioxolan-2-yl)acetaldehyde (320 mg, 2.459 mmol) and (3-bromo-5-nitro-4-pyridyl)hydrazine (286.4 mg, 1.229 mmol) were heated under reflux in ethanol (2.864 mL) overnight. The reaction mixture was concentrated in vacuo and the residue was partitioned between DCM and a saturated aqueous sodium hydrogen carbonate solution. Combined organic extract was dried over MgSO4 and concentrated in vacuo to leave 3-bromo-4-(5-methyl-1H-pyrazol-1-yl)-5-nitropyridine as a yellow oil. (200 mg, 85%). MS (ES+) 284.9.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between DCM
  3. extractionCombined organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28d38fbbce2f4f7fbd1058e1a32f35c4
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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