Sodium Iodide → 1-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-3-nitro-1H-pyrazole

HRID 1946348Notes

Reaction equation

HRID 1946348 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[Cl:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:19]([CH2:18][N:6]2[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]2)[CH:24]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 221055531-(Benzyloxy)-2-(bromomethyl)-4-chlorobenzeneHCID 178526745HCID 178526745, compound

Product 1

HCID 595479671-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-3-nitro-1H-pyrazoleYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Nitro-1H-pyrazole (Fluorochem) (0.505 g, 4.47 mmol) was dissolved in DMF (10 ml). Potassium carbonate (0.973 g, 7.04 mmol) and sodium iodide (75 mg, 0.50 mmol) were added. 2-(Bromomethyl)-4-chloro-1-[(phenylmethyl)oxy]benzene (WO2006066968) (1.33 g, 4.25 mmol) was added and washed in with further DMF (10 ml). The reaction was stirred at room temperature for 30 min, then concentrated in vacuo. The crude material was treated with water (150 ml). The aqueous mixture was extracted with EtOAc (3×150 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified on silica (70 g) using 0-100% EtOAc-cyclohexane. Appropriate fractions were concentrated in vacuo to give the title compound as a yellow solid (952 mg);

Workup

  1. washwashed in with further DMF (10 ml)
  2. concentrationconcentrated in vacuo
  3. additionThe crude material was treated with water (150 ml)
  4. extractionThe aqueous mixture was extracted with EtOAc (3×150 ml)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica (70 g)
  8. concentrationAppropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-62fb8a9bbc1e44a39e917f85edf5c169
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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