Dimethylformamide → 3-Methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]imidazolidine-2,4-dione

HRID 2281045Notes

Reaction equation

[B:1]1([C:10]2[CH:15]=[CH:14][C:13]([CH2:16]Br)=[CH:12][CH:11]=2)[O:5][C:4]([CH3:7])([CH3:6])[C:3]([CH3:9])([CH3:8])[O:2]1.[CH3:18][N:19]1[C:23](=[O:24])[CH2:22][NH:21][C:20]1=[O:25].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[CH3:18][N:19]1[C:23](=[O:24])[CH2:22][N:21]([CH2:16][C:13]2[CH:14]=[CH:15][C:10]([B:1]3[O:5][C:4]([CH3:7])([CH3:6])[C:3]([CH3:9])([CH3:8])[O:2]3)=[CH:11][CH:12]=2)[C:20]1=[O:25]

Participants

Conditions

Temperature: 45 °C

Procedure

2-[4-(Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaboronate (5.00 g, 16.84 mmol), 3-methylimidazolidine-2,4-dione (2.11 g, 18.52 mmol, 1.1 equiv) and potassium carbonate (4.65 g, 33.7 mmol, 2 equiv) were combined and treated with N,N-dimethylformamide (17 mL). The mixture heated for 3 hours at 45° C., cooled to ambient temperature, diluted with ethyl acetate and washed with water (3×) and brine. The organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo to afford the titled compound.

Workup

temperaturecooled to ambient temperature
washwashed with water (3×) and brine
dry with materialThe organic extracts were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-99778bbd385a450dad128757ba515140
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139576B2

Reaction notes

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