1-Bromopropane → HCID 19616496, compound

HRID 600989Notes

Reaction equation

HRID 600989 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:12][CH2:13][CH3:14]>CN(C)C=O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:12][CH2:13][CH3:14])[N:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 178526745HCID 178526745, compound

Product 1

HCID 19616496HCID 19616496, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Nitro-1H-pyrazole (prepared as in Example 15, 100 mg, 0.89 mmol) was dissolved in anhydrous N,N-dimethylformamide (4 mL) and a 60% dispersion of sodium hydride in mineral oil (37 mg, 0.93 mmol) was added while stirring under nitrogen. After the effervescence ceased and the mixture stirred for an additional 10 min, the 1-bromo-propane (91 μL, 1.00 mmol) was added. The mixture continued to stir under nitrogen for 16 h. The solution was diluted with ethyl acetate (50 mL), washed with water (2×20 mL), saturated aqueous brine solution (2×20 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 10 g; 25% ethyl acetate/hexanes to 75% ethyl acetate/hexanes) afforded 3-nitro-1-propyl-1H-pyrazole (92 mg, 67%) as a yellow oil: H1-NMR (400 MHz, CDCl3) δ 0.89 (3H, t, J=7.6 Hz), 1.90 (2H, sextet, J=7.2 Hz), 6.82 (1H, d, J=2.8 Hz), 7.44 (1H, d, J=2.4 Hz).

Workup

  1. stirringthe mixture stirred for an additional 10 min
  2. stirringto stir under nitrogen for 16 h
  3. washwashed with water (2×20 mL), saturated aqueous brine solution (2×20 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 10 g; 25% ethyl acetate/hexanes to 75% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8a52aa03620f419b8a0334cb3ba7da55
Source dataset
uspto-grants-2011_03
Patent number
US07902248B2

Reaction notes

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