Methyl iodide → HCID 67491844, compound

HRID 711089Notes

Reaction equation

HRID 711089 reaction equation
[OH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[N:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:3]=1.[C:20](=O)([O-])[O-].[Cs+].[Cs+].CI>CC(C)=O>[CH3:20][O:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[N:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178473416HCID 178473416, compound

Product 1

HCID 67491844HCID 67491844, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Ethyl 6-methyl 3-hydroxy-1H-indazole-1,6-dicarboxylate (1.35 g, 5.11 mmol) was suspended in acetone (65 mL). Cesium carbonate (1.75 g, 5.36 mmol) and methyl iodide (1.0 mL, 15 mmol) were added and the reaction was heated to reflux for 23 hours. The reaction was concentrated to dryness. The residue was taken up in dichloromethane (100 mL) and water (100 mL). The layers were separated and the aqueous was extracted again with dichloromethane. The combined organics were dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography gave two regioisomeric products.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 23 hours
  3. concentrationThe reaction was concentrated to dryness
  4. customThe layers were separated
  5. extractionthe aqueous was extracted again with dichloromethane
  6. dry with materialThe combined organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash column chromatography
  10. customgave two regioisomeric products

Sources & evidence

ORD record
ord-7b08c560ba9841438bb5933845ab62f3
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

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