Ethyl isocyanate → 1-Ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

HRID 1626658Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[B:9]1[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]1)[NH2:5].[CH2:18]([N:20]=[C:21]=[O:22])[CH3:19].[N-]=C=O>C(Cl)Cl>[CH2:18]([NH:20][C:21]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[C:2]([F:1])[CH:3]=1)=[O:22])[CH3:19]

Participants

Conditions

Temperature: 35 °C

Procedure

To a stirred solution of 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.5 g, 6.33 mmol) in DCM (30 ml) was added ethyl isocyanate (1503 μL, 19 mmol). Reaction mixture was stirred at 35° C. for 20 hours. Additional isocyanate was added and reaction mixture left for sufficient time to ensure reaction completion. The crude reaction mixture was then partitioned between water and DCM. The organic layer was recovered, passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by flash chromatography using 0-60% ethyl acetate/petroleum ether 40-60 to yield a yellow solid (1.054 g, 3.42 mmol, 54%).

Workup

customReaction mixture
customreaction mixture
waitleft for sufficient time
customreaction completion
customThe crude reaction mixture
customwas then partitioned between water and DCM
customThe organic layer was recovered
customthe solvent removed in vacuo
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-00e47ba574064dfa8b03abd951223435
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785457B2

Reaction notes

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