Cesium carbonate → HCID 18701986, compound

HRID 2289131Notes

Reaction equation

HRID 2289131 reaction equation
[CH:1]1([C:4]2[C:8]3[CH:9]=[CH:10][C:11]([OH:16])=[C:12]([CH2:13][CH2:14][CH3:15])[C:7]=3[O:6]N=2)[CH2:3][CH2:2]1.ClC1C=C(CC(OC)=[O:31])C=CC=1NCCCBr.C(=O)([O-])[O-].[Cs+].[Cs+].CCCCCC.C(OCC)(=O)C>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([C:4]([C:8]2[CH:9]=[CH:10][C:11]([OH:16])=[C:12]([CH2:13][CH2:14][CH3:15])[C:7]=2[OH:6])=[O:31])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 18701920HCID 18701920, compoundHCID 21226206Ethyl acetate hexaneHCID 136413070HCID 136413070, compound

Product 1

HCID 18701986HCID 18701986, compoundYield 128.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-cyclopropyl-6-hydroxy-7-propylbenz-[4,5]-isoxazole (34 mg, 0.156 mmole) and methyl 3-chloro-4-(3-bromopropylamino)phenylacetate (Example 21, Step C, 50 mg, 0.156 mmole) in DMF (0.70 mL) was added cesium carbonate (54 mg , 0.164 mmole), and the mixture stirred at 80° C. in a nitrogen atmosphere for 2 hours. The cooled mixture was dissolved in ethyl acetate and washed with water, brine, dried over magnesium sulfate and concentrated in vacuo to give an oil. Thin layer chromatography on silica gel eluting with hexane:ethyl acetate (2:1) afforded the title compound (44 mg).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give an oil

Sources & evidence

ORD record
ord-8edb49c6ee49498fb037833de4e3e858
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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