Cesium carbonate → HCID 58136579, compound

HRID 877242Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[C:4](=[O:13])[NH:5][C:6]2=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:24][CH:23]=1>CN(C=O)C>[CH:36]1([CH:28]([C:25]2[CH:26]=[CH:27][C:22]([CH2:21][N:5]3[C:4](=[O:13])[C:3]4[C:7](=[C:8]([F:11])[CH:9]=[CH:10][C:2]=4[F:1])[C:6]3=[O:12])=[CH:23][CH:24]=2)[C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

Conditions

Temperature: 60 °C

Procedure

500 mg (2.71 mmol) of 4,7-difluoro-1H-isoindole-1,3(2H)-dione and 889.7 mg (2.71 mmol) of cesium carbonate were added to a solution of 964.7 mg (2.71 mmol) of tert-butyl(+/−)-[4-(bromomethyl)phenyl](cyclopentyl)acetate in 2 ml of DMF. The mixture was stirred at 60° C. for 2 h, and the reaction mixture was then added to ice-water. The mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution and dried over magnesium sulfate. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 5:1). This gave 424 mg (34.1% of theory) of the target compound.

Workup

extractionThe mixture was extracted three times with ethyl acetate
washThe combined organic phases were washed with saturated sodium chloride solution
dry with materialdried over magnesium sulfate
customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 5:1)

Sources & evidence

ORD record: ord-adfb4037157848e39e28a53e02dbff70
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987256B2

Reaction notes

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