Water → HCID 59497465, compound

HRID 1747419Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH:5]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]1=[O:18])[CH2:6][O:7][CH3:8].[I-].[CH3:21][N:22]1[C:30]2[C:25](=[C:26]([CH3:31])[CH:27]=[CH:28][CH:29]=2)[C:24]([CH2:32][N+](C)(C)C)=[CH:23]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH:5]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:32][C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])[N:22]([CH3:21])[CH:23]=2)[C:10]1=[O:18])[CH2:6][O:7][CH3:8]

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

temperatureThe solution is cooled down
extractionThe mixture is extracted with EtOAc (3×50 mL)
washwashed with water (3×100 mL)
dry with materialdried with MgSO4
concentrationconcentrated
customto give crude product
customPurification by flash column chromatography

Sources & evidence

ORD record: ord-81ea3b9b42bc4feeaf5b232bf8e0b3f1
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

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