Potassium Carbonate → HCID 10478188, compound

HRID 227271Notes

Reaction equation

C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([CH2:10]Br)[CH:7]=[CH:6][C:5]=1[O:12][CH3:13].[CH2:15]([O:17][CH2:18][CH2:19][N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:21]1)[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CC(CC(C)C)=O>[CH2:15]([O:17][CH2:18][CH2:19][N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH:29]2[CH2:30][CH2:31][N:32]([CH2:10][C:8]3[CH:7]=[CH:6][C:5]([O:12][CH3:13])=[C:4]([CH:9]=3)[C:3]([OH:2])=[O:14])[CH2:33][CH2:34]2)=[CH:21]1)[CH3:16]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 1.9 g (0.0071 mol) of 5-bromomethyl-2-methoxy-benzoic acid methyl ester in 5 ml of methyl isobutylketone was added to a suspension of 1.8 g (0.065 mol) of 1-(2-ethoxyethyl)-3-piperidin-4-yl-1H-indole and 1.8 g (0.013 mol) of potassium carbonate in 45 ml of methyl isobutylketone. The reaction mixture was heated at 60° C. for 20 h. The crude mixture was filtered to remove inorganic salts and the solvent was removed under reduced pressure affording 3.5 g of a crude oil. The crude mixture was purified by flash chromatography over silica gel affording 1.8 g (48% of yield) of 5-{4-[1-(2-ethoxyethyl)-1H-indol-3-yl]-piperidin-1-ylmethy}-2-methoxy-benzoic acid ethyl ester. This ester was dissolved in 18 ml of ethanol and hydrolysed with 2N NaOH at room temperature for 20 hours. The crude mixture was neutralised with 2N HCl aqueous solution and the solvent was removed under reduced pressure. The crude residue was extracted between dichloromethane and water. After drying, filtering and removing the solvent under reduced pressure, the residue obtained was recrystallised with ethanol affording 0.77 g (27% of overall yield) of the expected acid.

Workup

filtrationThe crude mixture was filtered
customto remove inorganic salts
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-a4cd932c0145488dae84ba6a7f0d5d75
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560471B2

Reaction notes

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