Cesium carbonate → HCID 67316346, compound

HRID 533269Notes

Reaction equation

HRID 533269 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]2[Br:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][CH2:26][CH2:27][O:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:25][CH2:26][CH2:27][O:28][C:29]1[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][CH:30]=1)[C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]2[Br:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 129593811-(3-Bromopropoxy)naphthaleneHCID 22676785HCID 22676785, compound

Product 1

HCID 67316346HCID 67316346, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 135A (500 mg) and 1-(3-bromopropoxy)naphthalene (354 mg) in N,N-dimethylformamide (10 ml) was added Cs2CO3 (871 mg). The reaction was stirred at room temperature overnight, diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography, eluting with 0%-50% dichloromethane in hexane, to provide the desired product.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 0%-50% dichloromethane in hexane

Sources & evidence

ORD record
ord-0419438948414758bac65625897815bd
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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