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

HRID 1747402Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12]2=[O:20])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[I-].[CH3:23][N:24]1[C:32]2[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=2)[C:26]([CH2:34][N+](C)(C)C)=[CH:25]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH2:34][CH:26]3[C:27]4[C:32](=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:33])[N:24]([CH3:23])[CH2:25]3)[C:12]2=[O:20])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of [1-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-cyclohexyl]-acetic acid methyl ester (115 mg, 0.40 mmol) and (1,4-dimethyl-1H-indol-3-ylmethyl)-trimethylammonium iodide (200 mg, 0.58 mmol) in DMF (2.5 mL) was added K2CO3 (110 mg, 0.80 mmol). The mixture was stirred at 100° C. for 4 hours. The reaction mixture was 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 30% EtOAc in Hexane as the eluent to afford the desired {1-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-cyclohexyl}-acetic acid methyl ester (131 mg, 74%).

Workup

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 30% EtOAc in Hexane as the eluent

Sources & evidence

ORD record: ord-13a3325e37024f94ad973445cac722b1
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

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