Cesium carbonate → methyl {5-[3-(4-cyano-2-propylphenoxy)propoxy]-1H-indol-1-yl}acetate

HRID 2424961Notes

Reaction equation

HRID 2424961 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH2:11][CH3:12].[CH3:13][O:14][C:15](=[O:31])[CH2:16][N:17]1[C:25]2[C:20](=[CH:21][C:22]([O:26][CH2:27][CH2:28][CH2:29]Br)=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:13][O:14][C:15](=[O:31])[CH2:16][N:17]1[C:25]2[C:20](=[CH:21][C:22]([O:26][CH2:27][CH2:28][CH2:29][O:1][C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=3[CH2:10][CH2:11][CH3:12])=[CH:23][CH:24]=2)[CH:19]=[CH:18]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 139876694-hydroxy-3-propylBenzonitrileHCID 57845410methyl [5-(3-bromopropoxy)-1H-indol-1-yl]acetate

Product 1

HCID 70971790methyl {5-[3-(4-cyano-2-propylphenoxy)propoxy]-1H-indol-1-yl}acetateYield 23.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-hydroxy-3-propylbenzonitrile (Example 33, 1.33 g, 8.28 mmol) and methyl[5-(3-bromopropoxy)-1H-indol-1-yl]acetate (Example 47, 2.70 g, 8.28 mmol) in DMF (50 mL, containing 1% water), was added cesium carbonate (5.39 g, 16.55 mmol). The mixture was stirred at rt for 24 h and then the solvent was evaporated under reduced pressure. The residue was suspended in ethyl acetate and filtered. The filtrate was concentrated and purified via silica gel column chromatography (0-10% EtOAc in hexanes) to give 787 mg (23%) of the product as a solid. This was used in later steps with no further purification.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified via silica gel column chromatography (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-42497257f542415e89e91064ea5feea5
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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