Potassium Carbonate → HCID 86681706, compound

HRID 571299Notes

Reaction equation

[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:9]2=[O:24])(=[O:4])=[O:3].C([O-])([O-])=O.[K+].[K+].Cl[CH2:32][C:33]1[S:34][CH:35]=[CH:36][CH:37]=1>C(#N)C>[O:15]=[C:11]1[C:12]2[C:8](=[CH:7][C:6]([N:5]([CH2:32][C:33]3[S:34][CH:35]=[CH:36][CH:37]=3)[S:2]([CH3:1])(=[O:3])=[O:4])=[CH:14][CH:13]=2)[C:9](=[O:24])[N:10]1[CH2:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of tert-butyl 2-(5-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (500 mg, 1.411 mmol) (prepared in an analogous manner as previously described in Example 34, Scheme 34, Steps 1, 2, 3) in acetonitrile (10 ml), K2CO3 (390 mg, 2.82 mmol) and 2-(chloromethyl)thiophene (281 mg, 2.116 mmol) (obtainable as described in U.S. Pat. No. 5,716,943, which is incorporated herein by reference in its entirety) were added, and the reaction was heated under microwave irradiation at 120° C. for 3 hours. The mixture was filtered and the filtrate was evaporated to dryness. The resulting crude was purified by flash chromatography on silica gel (hexane/EtOAc 2/1) affording tert-butyl 2-(1,3-dioxo-5-(N-(thiophen-2-ylmethyl)methylsulfonamido)-isoindolin-2-yl)acetate (600 mg, 1.332 mmol, 94% yield, MS/ESI+ 472.9 [MNa]+).

Workup

additionwere added
filtrationThe mixture was filtered
customthe filtrate was evaporated to dryness
customThe resulting crude was purified by flash chromatography on silica gel (hexane/EtOAc 2/1)

Sources & evidence

ORD record: ord-653f3a5f7b314c9298c585da2ab85cc1
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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