Cesium carbonate → ethyl ((1S)-5-{3-[(3-methyl-7-propyl-1,2-benzisoxazol-6-yl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

HRID 2235878Notes

Reaction equation

HRID 2235878 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([OH:14])=[C:10]([CH2:11][CH2:12][CH3:13])[C:5]=2[O:4][N:3]=1.[CH2:15]([O:17][C:18](=[O:34])[CH2:19][C@H:20]1[C:28]2[C:23](=[CH:24][C:25]([O:29][CH2:30][CH2:31][CH2:32]Br)=[CH:26][CH:27]=2)[CH2:22][CH2:21]1)[CH3:16].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:15]([O:17][C:18](=[O:34])[CH2:19][C@H:20]1[C:28]2[C:23](=[CH:24][C:25]([O:29][CH2:30][CH2:31][CH2:32][O:14][C:9]3[CH:8]=[CH:7][C:6]4[C:2]([CH3:1])=[N:3][O:4][C:5]=4[C:10]=3[CH2:11][CH2:12][CH3:13])=[CH:26][CH:27]=2)[CH2:22][CH2:21]1)[CH3:16]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 16110497ethyl[(1S)-5-(3-bromopropoxy)-2,3-dihydro-1H-inden-1-yl]acetateHCID 1360297883-Methyl-7-propyl-1,2-benzisoxazol-6-ol

Product 1

HCID 59300521ethyl ((1S)-5-{3-[(3-methyl-7-propyl-1,2-benzisoxazol-6-yl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetateYield 44.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-methyl-7-propyl-1,2-benzisoxazol-6-l (269 mg, 1.01 mmol) (Example 67) and ethyl[(1S)-5-(3-bromopropoxy)-2,3-dihydro-1H-inden-1-yl]acetate (331 mg, 1.01 mmol) (Example 45) in DMF (8 mL, containing 1 vol % water) was added Cs2CO3 (661 mg, 2.03 mmol). The mixture was stirred for 16 h at rt, and then the reaction mixture was concentrated under reduced pressure. The residue was suspended in EtOAc and filtered through a small plug of silica to give 204 mg (39%) of the title compound as a white solid that was used in the next step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. filtrationfiltered through a small plug of silica

Sources & evidence

ORD record
ord-7f89f94a42f24c259dce2fa951ede27e
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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