Water → HCID 59497288, compound

HRID 1747429Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19].[I-].[CH3:22][N:23]1[C:31]2[C:26](=[C:27]([CH3:32])[CH:28]=[CH:29][CH:30]=2)[C:25]([CH2:33][N+](C)(C)C)=[CH:24]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:33][C:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[N:23]([CH3:22])[CH:24]=2)[C:11]1=[O:19]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-benzoic acid methyl ester (30 mg, 0.11 mmol) in DMF (1.0 mL) are added (1,4-Dimethyl-1H-indol-3-ylmethyl)-trimethyl-ammonium iodide (46 mg, 0.13 mmol) and K2CO3 (31 mg, 0.22 mmol) at room temperature. The solution is heated to 60° C. for 16 hr and it is cooled down to room temperature for another 48 hr. Then 30 mL of water is added. The mixture is extracted with EtOAc (3×30 mL) and the combined organic layers are washed with water (3×100 mL), dried with Na2SO4 and concentrated to give crude product. Purification by preparative TLC affords 40 mg (86%) of 2-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-benzoic acid methyl ester.

Workup

temperatureit is cooled down to room temperature for another 48 hr
extractionThe mixture is extracted with EtOAc (3×30 mL)
washthe combined organic layers are washed with water (3×100 mL)
dry with materialdried with Na2SO4
concentrationconcentrated
customto give crude product
customPurification by preparative TLC

Sources & evidence

ORD record: ord-1df71cbbfa8d47d99a35928dc1b4a6af
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

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