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 603407Notes

Reaction equation

HRID 603407 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.Br[CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[C@H:25]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:24][CH2:23]2.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:14][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[C@H:25]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:24][CH2:23]4)=[C:10]([CH2:11][CH2:12][CH3:13])[C:5]=2[O:4][N:3]=1

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-ol (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-1c298b2b4364485c81484657539943cb
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

Loading…