Sodium hydride → HCID 19621838, compound

HRID 546017Notes

Reaction equation

HRID 546017 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH:12]([OH:15])[CH2:13][CH3:14]>CN(C)C=O>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:14][CH2:13][CH2:12][OH:15])[N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12887879BromopropanolHCID 178526745HCID 178526745, compound

Product 1

HCID 19621838HCID 19621838, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-nitro-1H-pyrazole (prepared in example 3, 200 mg, 1.77 mmol) in anhydrous N,N-dimethylformamide (2 mL), a 60% dispersion of sodium hydride in mineral oil (92 mg, 2.30 mmol) was added while stirring under nitrogen. After the effervescence ceased and the mixture was stirred for an additional 30 min, bromopropanol (208 μL, 2.30 mmol) was added. The mixture was continued to stir under nitrogen for an additional 2 h. The solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 2% methanol/methylene chloride to 5% methanol/methylene chloride) afforded 3-(3-nitro-pyrazol-1-yl)-propan-1-ol (144 mg, 48%) as an oil: H1-NMR (400 MHz, CDCl3) δ 2.09 (2H, m), 2.84 (1H, s), 3.60 (2H, t, J=5.8 Hz), 4.32 (2H, t, J=6.8 Hz), 6.82 (1H, D, J=2.4 Hz), 7.51 (1H, d, J=2.4 Hz).

Workup

  1. stirringthe mixture was stirred for an additional 30 min
  2. stirringto stir under nitrogen for an additional 2 h
  3. customThe solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 2% methanol/methylene chloride to 5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-ed383ba724f244aea7fa37958345d172
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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