Water → ethyl ((1S)-5-{3-[(3-methyl-1-benzofuran-6-yl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

HRID 603403Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 6-(3-bromopropoxy)-3-methyl-1-benzofuran (87 mg, 0.32 mmol) (Example 63) and ethyl [(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (59 mg, 0.269 mmol) (Example 6) in DMF containing 1 vol % water (2.4 mL) was added Cs2CO3 (105 mg, 0.323 mmol). The mixture was stirred for 68 h at 80° C., and the reaction mixture cooled to rt, then concentrated under reduced pressure. The residue was suspended in EtOAc and filtered through a small plug of silica to give 119 mg (90%) of a light-yellow solid that was used in the next step without further purification.

Workup

temperaturethe reaction mixture cooled to rt
concentrationconcentrated under reduced pressure
filtrationfiltered through a small plug of silica

Sources & evidence

ORD record: ord-d6e1f8c7da5d4a9abe18f94c610f0549
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906653B2

Reaction notes

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