Potassium Carbonate → 3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-6-methyl-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester

HRID 1747310Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:20])[CH2:7][CH2:8][CH3:9])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:28][N:29]1[C:37]2[C:32](=[C:33]([CH3:38])[CH:34]=[CH:35][CH:36]=2)[C:31]([CH2:39][N+](C)(C)C)=[CH:30]1.[I-]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:13]=2[N:12]([CH2:39][C:31]2[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])[N:29]([CH3:28])[CH:30]=2)[C:11]1=[O:20])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(6-Methyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl ester (50 mg, 0.17 mmol) in DMF (2 mL) were added K2CO3 (71 mg, 0.52 mmol) and (1,4-Dimethyl-1H-indol-3-ylmethyl)-trimethyl-ammonium; iodide (90 mg, 0.26 mmol). The reaction mixture was heated to 80° C. for 16 h. The reaction mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was then dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 4:1 Hexanes:ethyl acetate as an eluent to afford 35 mg of the desired product as oil. LCMS (ESMS): m/z 448.82 (M+H+).

Workup

washwashed with water (×4)
dry with materialThe organic phase was then dried over Na2SO4
concentrationconcentrated
customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record: ord-275f7428191a41748ca545397b26a332
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

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