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 1477920Notes

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-90a43a2826e04d57a47681a705b208d5
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403807B2

Reaction notes

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