Cesium carbonate → (R)-4-((R)-1-(5-bromo-1,2-dimethyl-1H-benzo[d]imidazol-7-yloxy)ethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one

HRID 2209173Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 5-bromo-1-methyl-1H-benzo[d]imidazol-7-ol (30 mgs, 0.124 mmol) in DMF (3 mL) was added (S)-1-((R)-5-oxo-1-((R)-1-phenylethyl)pyrrolidin-3-yl)ethyl methanesulfonate 1.17 (60 mgs, 0.193 mmol) and Cs2CO3 (69 mgs, 0.212 mmol) and the reaction mixture was heated at 90° C. for 1 h. The reaction mixture was then diluted with ethylacetate and washed with water (3×), brine and dried over anhydrous magnesium sulfate. Filtration, followed by concentration gave (R)-4-((R)-1-(5-bromo-1,2-dimethyl-1H-benzo[d]imidazol-7-yloxy)ethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one, which was used for next step without further purification.

Workup

washwashed with water (3×), brine
dry with materialdried over anhydrous magnesium sulfate
filtrationFiltration
concentrationfollowed by concentration

Sources & evidence

ORD record: ord-2f9047b114a648c88c3a3d570305c3bd
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Reaction notes

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