Potassium Carbonate → 3-[3-(5-Chloro-1,2,3-trimethyl-1H-indol-7-ylmethyl)-6-methyl-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid methyl ester

HRID 1747314Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=4[NH:14][C:13]3=[O:22])[CH:10]=1)[N:7]([CH3:23])[C:6]([CH3:24])=[C:5]2[CH3:25].[C:26]([O:32][CH3:33])(=[O:31])[CH:27]=[CH:28][CH2:29][CH3:30].C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.C(OCC)(=O)C>[CH3:33][O:32][C:26](=[O:31])[CH2:27][CH:28]([N:14]1[C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2[N:12]([CH2:11][C:9]2[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:8]=2[N:7]([CH3:23])[C:6]([CH3:24])=[C:5]3[CH3:25])[C:13]1=[O:22])[CH2:29][CH3:30]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 1-(5-Chloro-1,2,3-trimethyl-1H-indol-7-ylmethyl)-5-methyl-1,3-dihydro-benzimidazol-2-one (40 mg, 0.11 mmol) in DMA (2 mL) were added Methyl 2-pentenoate (26 mg, 0.23 mmol) and K2CO3 (31 mg, 0.23 mmol). The reaction mixture was heated to 120° C. for 20 min in a microwave. When the reaction was completed, the reaction mixture was diluted with ethyl acetate and washed with water (×4). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 4:1 Hexane:ethyl acetate to afford 40 mg of the desired product. LCMS (ESMS): m/z 468.36 (M+H+).

Workup

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

Sources & evidence

ORD record: ord-85c7820eebb94792b8428e3a22a7b79b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

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