2-Bromoethanol → HCID 86681721, compound

HRID 571313Notes

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][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:9]2=[O:27])(=[O:4])=[O:3].C([O-])([O-])=O.[K+].[K+].Br[CH2:35][CH2:36][OH:37]>C(#N)C>[OH:37][CH2:36][CH2:35][N: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][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:9]2=[O:27])[S:2]([CH3:1])(=[O:3])=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of benzyl 2-(5-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (0.700 g, 1.802 mmol) in acetonitrile (20 ml), K2CO3 (0.498 g, 3.605 mmol) and 2-bromoethanol (0.509 ml, 7.21 mmol) were further added. The mixture was heated under MW irradiation at 110° C. for 2 hours. 2-Bromoethanol (0.272 ml, 3.734 mmol) and K2CO3 (0.268 g, 1.931 mmol) were added, and the reaction was heated under MW irradiation at 110° C. for additional 3 hours. The mixture was then diluted with acetonitrile, the insoluble inorganic salts were filtered off and the filtrate was evaporated to dryness. The crude was purified by trituration with Et2O affording benzyl 2-(5-(N-(2-hydroxyethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (0.746 g, 1.725 mmol, 96% yield, MS/ESI+ 432.9 [MH]+).

Workup

temperaturethe reaction was heated under MW irradiation at 110° C. for additional 3 hours
filtrationthe insoluble inorganic salts were filtered off
customthe filtrate was evaporated to dryness
customThe crude was purified by trituration with Et2O

Sources & evidence

ORD record: ord-28f38b7dd29c4b42bfe77863c910e7a5
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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