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

HRID 1771527Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:12])([CH3:11])[O:9]2)=[C:4]([F:17])[CH:3]=1.[N:18]([CH:21]1[CH2:23][CH2:22]1)=[C:19]=[O:20]>C(Cl)Cl>[CH:21]1([NH:18][C:19]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([B:8]3[O:9][C:10]([CH3:12])([CH3:11])[C:13]([CH3:15])([CH3:14])[O:16]3)=[C:4]([F:17])[CH:3]=2)=[O:20])[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 37 °C

Procedure

To a stirred solution of 4-amino-2-fluorophenyl boronic acid pinacol ester (1.185 g, 5.0 mmol) in DCM (17 ml) was added isocyanato cyclopropane (830 mg, 10.0 mmol) and stirred overnight at 37° C. The reaction mixture was washed with water (20 mL), passed through a PTFE hydrophobic frit and the solvent removed in vacuo to yield a white solid (1.56 g) used without further purification.

Workup

washThe reaction mixture was washed with water (20 mL)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-693c58a3f3524363b319c1620a252461
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249129B2

Reaction notes

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