Sodium hydride → HCID 68784897, compound

HRID 1441299Notes

Reaction equation

HRID 1441299 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH3:11].[H-].[Na+].Cl[CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([O:16][CH2:15][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[C:5]([CH3:11])=[N:6]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 178434225HCID 178434225, compound

Product 1

HCID 68784897HCID 68784897, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. stirred solution of 5-bromo-3-methyl-indazole (from Preparation 1, 1.00 g, 4.33 mmol) in anhydrous DMF (30 mL) under nitrogen was added sodium hydride (60% in mineral oil, 0.21 g, 5.19 mmol). After 30 min, benzyl chloromethyl ether (60%, 1.47 g, 5.63 mmol) was added vial syringe in about 1 min. Stirring was continued for 1 h. The mixture was poured into ice water (100 mL) and extracted with ethyl acetate. The combined extracts were dried, filtered and concentrated to give an oil that was purified by chromatography on silica gel (hexane/ethyl acetate 10:1) to give the title compound (0.72 g, 50%) that was pure by NMR.

Workup

  1. waitwas continued for 1 h
  2. extractionextracted with ethyl acetate
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas purified by chromatography on silica gel (hexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-c6e50ee689ae4bcbb1a622baa1901ed9
Source dataset
uspto-grants-2010_02
Patent number
US07655662B2

Reaction notes

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