Chloromethyl Methyl Ether → HCID 68663776, compound

HRID 452595Notes

Reaction equation

HRID 452595 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Na+].Cl[CH2:17][O:18][CH3:19]>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH3:17][O:18][CH2:19][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

7

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 22260640Methyl 1H-indazole-5-carboxylate

Product 1

HCID 68663776HCID 68663776, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 1H-indazole-5-carboxylate (5.02 g, 28.5 mmol) in N,N-dimethylformamide (60 mL) was added sodium hydride (60% in oil, 1.26 g, 31.5 mmol) at room temperature, and the resulting mixture was stirred for 10 min. To this reaction mixture was added dropwise a solution of (chloromethyl)methylether (2.39 mL, 31.5 mmol) in tetrahydrofuran (20 mL) at −20° C. over 10 min, and the resulting mixture was allowed to warm to room temperature over 2 hr. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1), and crystallized from hexane/ethyl acetate to give the title compound (3.62 g, yield 58%) as colorless crystals.

Workup

  1. washwashed twice with water and once with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)
  5. customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-52628211da34484fbbdb6476f125a245
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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