Potassium Carbonate → 4-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid methyl ester

HRID 1747397Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 4-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-pentanoic acid methyl ester (85 mg, 0.34 mmol) and (1,4-dimethyl-1H-indol-3-ylmethyl)-trimethylammonium iodide (175 mg, 0.51 mmol) in DMF (2.5 mL) was added K2CO3 (95 mg, 0.69 mmol). The mixture was stirred at 100° C. for 4 hours. The reaction mixture was allowed to cool to room temperature, diluted with EtOAc (50 mL) and washed with H2O (50 mL×3). The organic layer was dried over sodium sulfate and concentrated. The resulting residue was purified by CombiFlash with 25% EtOAc in Hexane as the eluent to afford the desired 4-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid methyl ester (120 mg, 86%).

Workup

temperatureto cool to room temperature
washwashed with H2O (50 mL×3)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated
customThe resulting residue was purified by CombiFlash with 25% EtOAc in Hexane as the eluent

Sources & evidence

ORD record: ord-00e7819131bb4fe5a7321b2283b4d3c3
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

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