Cesium carbonate → HCID 68285057, compound

HRID 571603Notes

Reaction equation

HRID 571603 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:28])[N:14]([CH3:27])[N:15]=[C:16]([OH:26])[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2].I[CH2:30]CC.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:28])[N:14]([CH3:27])[N:15]=[C:16]([O:26][CH3:30])[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 178436240HCID 178436240, compound

Product 1

HCID 68285057HCID 68285057, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-(2,6-diethyl-4-methylphenyl)-6-hydroxy-5-benzyloxy-2-methyl-3(2H)-pyridazinone (500 mg, 2.35 mmol) in acetone (10 ml) was added iodopropane (443 mg, 2.59 mmol) and cesium carbonate (920 mg, 2.59 mmol), and stirred under reflux for 2.5 hours. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 643 mg of Compound (I-8-1) (yield: 70%).

Workup

  1. temperatureunder reflux for 2.5 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-6d07e3ecb85f49418f870bb6cdf385c5
Source dataset
uspto-grants-2015_05
Patent number
US09029295B2

Reaction notes

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