Methyl iodide → HCID 67491561, compound

HRID 711066Notes

Reaction equation

HRID 711066 reaction equation
[OH:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[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][N:3]1[C:2](=[O:1])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[N:4]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178473417HCID 178473417, compound

Product 1

HCID 67491561HCID 67491561, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Ethyl 5-methyl 3-hydroxy-1H-indazole-1,5-dicarboxylate (1.75 g, 6.62 mmol) was suspended in acetone (85 mL). Cesium carbonate (2.27 g, 6.95 mmol) and methyl iodide (1.3 mL, 20 mmol) were added and the reaction was stirred at reflux for 22 hours. The reaction was concentrated to dryness and the residue was partitioned between dichloromethane (60 mL) and water (100 mL). The layers were separated and the aqueous was extracted again with dichloromethane (60 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (7-60% ethyl acetate/heptanes) gave two regioisomeric products.

Workup

  1. temperatureat reflux for 22 hours
  2. concentrationThe reaction was concentrated to dryness
  3. customthe residue was partitioned between dichloromethane (60 mL) and water (100 mL)
  4. customThe layers were separated
  5. extractionthe aqueous was extracted again with dichloromethane (60 mL)
  6. dry with materialThe combined organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash column chromatography (7-60% ethyl acetate/heptanes)
  10. customgave two regioisomeric products

Sources & evidence

ORD record
ord-8b2cbf83489d41ddb380a26c05961ad6
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

Loading…