Azetidine → 5-(Azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole

HRID 1907798Notes

Reaction equation

HRID 1907798 reaction equation
Br[CH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[NH:12]1[CH2:15][CH2:14][CH2:13]1>C1COCC1>[N:12]1([CH2:2][C:3]2[N:7]([CH3:8])[N:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=2)[CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 585403565-(Bromomethyl)-1-methyl-3-nitro-1H-pyrazole

Product 1

HCID 585403155-(Azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazoleYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was charged with THF (45 mL), 20 (1.66 g, 7.54 mmol), azetidine (531 mg, 9.31 mmol) and stirred at room temperature for 24 h. After this time the reaction was concentrated to dryness under reduced pressure, and the resulting solid was diluted with a mixture of methylene chloride (15 mL) and 10% aqueous potassium carbonate (15 mL). The aqueous layer was separated and extracted with methylene chloride (2×15 mL). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 99% yield (1.47 g) of 21 as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 6.74 (s, 1H), 3.97 (s, 3H), 3.55 (s, 2H), 3.22 (t, 4H, J=7.2 Hz), 2.10 (pentet, 2H, J=7.2 Hz); MS (ESI+) m/z 197.1 (M+H).

Workup

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. concentrationAfter this time the reaction was concentrated to dryness under reduced pressure
  3. additionthe resulting solid was diluted with a mixture of methylene chloride (15 mL) and 10% aqueous potassium carbonate (15 mL)
  4. customThe aqueous layer was separated
  5. extractionextracted with methylene chloride (2×15 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-187485f1dd1143c8b0fa70c8b0c98dec
Source dataset
uspto-grants-2013_12
Patent number
US08598174B2

Reaction notes

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