Benzyl Bromide → HCID 178434287, compound

HRID 2423084Notes

Reaction equation

HRID 2423084 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([CH3:13])=[N:7][NH:8]2.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH3:13][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[CH:12][C:4]=2[O:3][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:8][N:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178434282HCID 178434282, compound

Product 1

HCID 178434287HCID 178434287, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (0.452 g of a 60% dispersion in mineral oil, 11.3 mmol) in DMF (30 mL) was added 4-hydroxy-3-methylindazole (1.52 g, 10.3 mmol) (prepared in a similar manner to that described in J. Med Chem., 2000, 2672) in DMF (20 mL) via a cannula. The mixture was stirred at room temperature for 10 minutes and then benzyl bromide (1.223 mL, 10.3 mmol) was added and stirring was continued at room temperature for 2 hrs. The mixture was quenched with ammonium chloride solution and the DMF was evaporated. Ethyl acetate and water were added and the product was extracted into ethyl acetate and the extracts were dried (Na2SO4) and evaporated. Chromatography (0-100% ethyl acetate in hexane) gave the title compound (D30) as an orange solid (1.774 g, containing ˜10% dibenzylated material).

Workup

  1. customprepared in a similar manner to that
  2. stirringstirring
  3. waitwas continued at room temperature for 2 hrs
  4. customThe mixture was quenched with ammonium chloride solution
  5. customthe DMF was evaporated
  6. additionEthyl acetate and water were added
  7. extractionthe product was extracted into ethyl acetate
  8. dry with materialthe extracts were dried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-b9a982fbab7d43009780d52b8d1e9386
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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