3-(4-Chlorophenyl)-3-(4-(methylsulfonamido)-1H-indol-1-yl)pentyl methanesulfonate → N-(1-(3-(4-Chlorophenyl)-1-methoxypentan-3-yl)-1H-indol-4-yl)methanesulfonamide

HRID 1427296Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of 3-(4-chlorophenyl)-3-(4-(methylsulfonamido)-1H-indol-1-yl)pentyl methanesulfonate (10 mg, 0.02 mmol), as described in Example 40 Step I, in methanol (2 mL) was added CH3ONa (21 mg, 0.4 mmol) at room temperature. Then the mixture was heated to 40° C. for 2 h. The solution was quenched with saturated ammonium chloride solution (10 mL), and extracted with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by Prep-HPLC (Mobile phase: acetonitrile/water (0.03% TFA)) to afford the title compound as a white solid. LC/MS m/z=421.1[M+H]+.

Workup

customThe solution was quenched with saturated ammonium chloride solution (10 mL)
extractionextracted with ethyl acetate
washThe organic layers were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
customThe residue was purified by Prep-HPLC (Mobile phase: acetonitrile/water (0.03% TFA))

Sources & evidence

ORD record: ord-e5dd01eda8374b00a267ebb7d78b86b7
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933113B2

Reaction notes

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