Potassium Carbonate → HCID 86681743, compound

HRID 571328Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of methyl 2-(5-(methylsulfonamido)-2-oxoindolin-1-yl)acetate (0.500 g, 1.607 mmol) (prepared in an analogous manner as described in Example 20, Scheme 20, Steps 1, 2, 3, 4), 4-(2-chloroethyl)morpholine hydrochloride (0.393 g, 2.112 mmol), and K2CO3 (0.524 g, 3.788 mmol) in DMF (25 ml) was heated at 65° C. for 2 hours. The mixture was partitioned between ethyl acetate and aqueous 5% NaHCO3; the organic phase was washed several times with brine and dried over sodium sulfate. The solvent was removed under vacuum and the dark crude was purified by flash chromatography on silica gel column (DCM:MeOH=99:1 to 97:3) affording methyl 2-(5-(N-(2-morpholinoethyl)methylsulfonamido)-2-oxoindolin-1-yl)acetate (0.100 g, 0.243 mmol, 14.5% yield, MS/ESI+ 412.0 [MH]+).

Workup

customprepared in an analogous manner
customThe mixture was partitioned between ethyl acetate and aqueous 5% NaHCO3
washthe organic phase was washed several times with brine
dry with materialdried over sodium sulfate
customThe solvent was removed under vacuum
customthe dark crude was purified by flash chromatography on silica gel column (DCM:MeOH=99:1 to 97:3)

Sources & evidence

ORD record: ord-212b43dd420e491cb2bb235586db3220
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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