4-Bromo-3-(1,3-dioxolan-2-yl)phenol → 2-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-6-(2-hydroxy-ethylamino)-nicotinonitrile

HRID 1483693Notes

Reaction equation

BrC1C=CC(OC2C=CC(C#N)=C(Cl)[N:8]=2)=CC=1C1OCCO1.[Br:23][C:24]1[CH:39]=[CH:38][C:27]([O:28][C:29]2[N:36]=[C:35](Cl)[CH:34]=[CH:33][C:30]=2[C:31]#[N:32])=[CH:26][C:25]=1[CH:40]1[O:44][CH2:43][CH2:42][O:41]1.BrC1C=C[C:49]([OH:52])=[CH:48]C=1C1OCCO1>C(#N)C>[Br:23][C:24]1[CH:39]=[CH:38][C:27]([O:28][C:29]2[N:36]=[C:35]([NH:8][CH2:48][CH2:49][OH:52])[CH:34]=[CH:33][C:30]=2[C:31]#[N:32])=[CH:26][C:25]=1[CH:40]1[O:44][CH2:43][CH2:42][O:41]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-(4-bromo-3-[1,3]dioxolan-2-yl-phenoxy)-2-chloro-nicotinonitrile and 2-(4-bromo-3-[1,3]dioxolan-2-yl-phenoxy)-6-chloro-nicotinonitrile, (4+5, 2.5 g, 6.6 mmol) in acetonitrile (anhydrous, 50 mL) was added 2-amino-ethanol (2) (3.96 g, 66 mmol). The reaction was heated at 80° C. for 2 hours. After the reaction cooled to room temperature, all volatile components were removed in vacuo. Purification was accomplished by silica gel chromatography, eluting with 25%-100% EtOAc/Hexane gradient, to give 1.1 g of title compound in 41% yield.

Workup

temperatureAfter the reaction cooled to room temperature
customall volatile components were removed in vacuo
customPurification
washeluting with 25%-100% EtOAc/Hexane gradient

Sources & evidence

ORD record: ord-75ac0e163fab49db8d045e21e79ebf9f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416146B2

Reaction notes

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