Cesium carbonate → HCID 67131202, compound

HRID 1890441Notes

Reaction equation

HRID 1890441 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.[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][C:23]2([O:25][CH2:24]2)[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][C:23]([OH:25])([CH2:24][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])[CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 299427567-Methoxyquinolin-2(1H)-oneHCID 42609244tert-Butyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate

Product 1

HCID 67131202HCID 67131202, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 7-methoxy-1H-quinolin-2-one (650 mg, 3.7 mmol) and 1-oxa-5-aza-spiro[2.4]heptane-5-carboxylic acid tert-butyl ester (1 eq., commercial) in DMF (10 mL) was treated with Cs2CO3 (1 eq.) and heated at 70° C. overnight. The mixture was partitioned between EA and water, the org. phase washed with water and brine, dried over MgSO4 and concentrated. The product was purified by CC (EA/Hept 1:1, EA) to give the desired intermediate as a yellowish oil (650 mg, 47% yield).

Workup

  1. customThe mixture was partitioned between EA and water
  2. washphase washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe product was purified by CC (EA/Hept 1:1, EA)

Sources & evidence

ORD record
ord-7578d55693fe4659bda49ccbec822be3
Source dataset
uspto-grants-2013_08
Patent number
US08507478B2

Reaction notes

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