Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | ((1,4-Dimethylindole-3-yl)methyl)trimethylammonium iodide | HCID 17836486 | — |
| Reactant | HCID 59497702 | HCID 59497702 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59497465 | HCID 59497465 | 61% |
Reaction Steps
To a solution of 4-Methoxy-3-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-butyric acid methyl ester (205 mg, 0.78 mmol) in DMF (10 mL) are added (1,4-Dimethyl-1H-indol-3-ylmethyl)-trimethyl-ammonium iodide (470 mg, 1.4 mmol) and K2CO3 (210 mg, 1.6 mmol) at room temperature. The solution is heated to 100° C. for 5.5 hours. The solution is cooled down and 30 mL of water is added. The mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined, washed with water (3×100 mL), dried with MgSO4 and concentrated to give crude product. Purification by flash column chromatography affords 200 mg (61%) of 3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-4-methoxy-butyric acid methyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150556B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-81ea3b9b42bc4feeaf5b232bf8e0b3f1 |
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| Source note | uspto-grants-2015_10 |
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