Cesium carbonate → (R)-4-((R)-1-(5-(3,4-dimethoxyphenyl)-1-methyl-1H-benzo[d]imidazol-7-yloxy)ethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one

HRID 2209021Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:20]=[C:19]([OH:21])[C:14]3[N:15]([CH3:18])[CH:16]=[N:17][C:13]=3[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CS(O[C@H:27]([C@@H:29]1[CH2:33][C:32](=[O:34])[N:31]([C@@H:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH3:36])[CH2:30]1)[CH3:28])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:20]=[C:19]([O:21][C@@H:27]([C@H:29]3[CH2:30][N:31]([C@@H:35]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH3:36])[C:32](=[O:34])[CH2:33]3)[CH3:28])[C:14]3[N:15]([CH3:18])[CH:16]=[N:17][C:13]=3[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 5-(3,4-dimethoxyphenyl)-1-methyl-1H-benzo[d]imidazol-7-ol 2.53 (42 mg, 0.148 mmol) in DMF (3 mL) was added (S)-1-((R)-5-oxo-1-((R)-1-phenylethyl)pyrrolidin-3-yl)ethyl methanesulfonate 1.17 (55 mg, 0.177 mmol) and Cs2CO3 (72 mg, 0.22 mmol) and the reaction mixture was heated at 90° C. for 2 h. The reaction mixture was concentrated and purified by flash chromatography (SiO2, 2% MeOH/EtOAc 25% MeOH/EtOAc) to give (R)-4-((R)-1-(5-(3,4-dimethoxyphenyl)-1-methyl-1H-benzo[d]imidazol-7-yloxy)ethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one 2.55.

Workup

concentrationThe reaction mixture was concentrated
custompurified by flash chromatography (SiO2, 2% MeOH/EtOAc 25% MeOH/EtOAc)

Sources & evidence

ORD record: ord-2702d208e75742a88a640410763526fb
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Reaction notes

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