Cesium carbonate → HCID 67316436, compound

HRID 533257Notes

Reaction equation

HRID 533257 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:6]2.Br[CH2:17][CH2:18][CH2:19][O:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O.CCOCC.O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:6]2[CH2:17][CH2:18][CH2:19][O:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 10989255Ethyl 4-bromo-1H-indole-2-carboxylateHCID 129593811-(3-Bromopropoxy)naphthalene

Product 1

HCID 67316436HCID 67316436, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of EXAMPLE 106A (5.5 g) in N,N-dimethylformamide (60 mL) was added 1-(3-bromopropoxy)naphthalene (5.4 g) and Cs2CO3 (22 g). The mixture was stirred overnight at room temperature. The mixture was diluted with ether (300 mL) and water (200 mL). The aqueous layer was extracted with ether twice. The combined extracts were washed with water (×3), brine and dried over Na2SO4. Concentration of the mixture gave crude product, which was purified by flash chromatography (2% ethyl acetate in hexane).

Workup

  1. extractionThe aqueous layer was extracted with ether twice
  2. washThe combined extracts were washed with water (×3), brine
  3. dry with materialdried over Na2SO4
  4. customConcentration of the mixture gave crude product, which
  5. customwas purified by flash chromatography (2% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0beeba05f1be42729f9f0b8214b9419d
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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