Sodium Azide → 5-(5-(azidomethyl)tetrahydrofuran-2-yl)-1-methyl-4-nitro-1H-pyrazole

HRID 521869Notes

Reaction equation

HRID 521869 reaction equation
I[CH2:2][CH:3]1[O:7][CH:6]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:5][CH2:4]1.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C.CCOC(C)=O>[N:17]([CH2:2][CH:3]1[O:7][CH:6]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:5][CH2:4]1)=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 867138175-(5-(iodomethyl)tetrahydrofuran-2-yl)-1-methyl-4-nitro-1H-pyrazole2×

Product 1

HCID 867138165-(5-(azidomethyl)tetrahydrofuran-2-yl)-1-methyl-4-nitro-1H-pyrazoleYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(5-(iodomethyl)tetrahydrofuran-2-yl)-1-methyl-4-nitro-1H-pyrazole (640 mg, 1.90 mmol, intermediate 60) in dry DMF (10 mL) was added sodium azide (250 mg, 3.80 mmol) and the mixture stirred at room temperature for 36 hr. The mixture was diluted with EtOAc (25 mL) and washed with water (2×10 mL) and brine (20 mL). The organic layer was passed through a phase separation cartridge and concentrated under reduced pressure to give 5-(5-(azidomethyl)tetrahydrofuran-2-yl)-1-methyl-4-nitro-1H-pyrazole as a yellow oil (480 mg, 100%). 1H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 5.84-5.70 (m, 1H), 4.49-4.45 (m, 1H), 4.03 (s, 3H), 3.56-3.39 (m, 2H), 2.66-2.65 (m, 1H), 2.29-2.22 (m, 1H), 2.02-1.92 (m, 2H).

Workup

  1. washwashed with water (2×10 mL) and brine (20 mL)
  2. customThe organic layer was passed through a phase separation cartridge
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46b1ac8dd8a640b2ba1075a6a5c7834e
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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