Cesium carbonate → HCID 68630090, compound

HRID 1801456Notes

Reaction equation

HRID 1801456 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.I[CH:15]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[C:22]([O:21][C:19]([N:17]1[CH2:18][CH:15]([N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH:7]=[CH:8][C:9]2=[O:13])[CH2:16]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateHCID 299427567-Methoxy-1,2-dihydroquinolin-2-one

Product 1

HCID 68630090HCID 68630090, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-methoxy-2(1H)-quinolinone (commercial; 290 mg; 1.65 mmol) and tert-butyl 3-iodo-1-azetidinecarboxylate (commercial; 391 mg; 1.38 mmol) and Cs2CO3 (613 mg; 1.88 mmol) in DMF (2 mL) was heated at 80° C. for 4 h. The reaction mixture was diluted with water and extracted with EA. The combined org. layers were washed with water and brine, dried over MgSO4, concentrated under reduced pressure and purified by CC (Hept/EA 1:1), affording a pale yellow oil (271 mg, 65% yield).

Workup

  1. extractionextracted with EA
  2. washlayers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by CC (Hept/EA 1:1)

Sources & evidence

ORD record
ord-be9ed1c053424608bb0e15b31c0f7660
Source dataset
uspto-grants-2013_01
Patent number
US08349826B2

Reaction notes

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