HCID 57968783, compound → HCID 67440681, compound

HRID 1471527Notes

Reaction equation

BrC1C=CC(OC2C=CC(C#N)=C(Cl)N=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=CC(OC2C=CC(C#N)=[C:53]([N:59]([CH2:61][CH2:62][O:63]C)C)N=2)=CC=1C=O>C(#N)C>[Br:23][C:24]1[CH:39]=[CH:38][C:27]([O:28][C:29]2[N:36]=[C:35]([N:59]([CH2:61][CH2:62][OH:63])[CH3:53])[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 compound mixture, 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, 1 g, 2.6 mmol) in acetonitrile (anhydrous, 30 mL) was added 2-methylamino-ethanol (6, 2.1 mL, 26 mmol). The reaction was heated at 80° C. for 2 hours. After the reaction, all volatile components were evaporated under vacuum. Purification was accomplished by silica gel chromatography, eluting with 10%-80% EtOAc/Hexane gradient, affording the title compound 400 mg in 36% yield. 1H NMR 400 MHz (CDCl3) δ 7.62 (d, J=8.6 Hz, 1H), 7.59 (d, J=8.6 Hz, 1H), 7.47 (d, J=3.1 Hz, 1H), 7.06 (dd, J=8.6 Hz, 3.1 Hz, 1H), 6.18 (d, J=8.6 Hz, 1H), 6.08 (s, 1H), 4.20-4.02 (m, 4H), 3.55 (t, J=3.2 Hz, 2H), 3.42 (t, J=3.2 Hz, 2H), 3.02 (s, 3H).

Workup

customAfter the reaction
customall volatile components were evaporated under vacuum
customPurification
washeluting with 10%-80% EtOAc/Hexane gradient

Sources & evidence

ORD record: ord-f79e3d7f550046f4825c11a0096926b6
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012431B2

Reaction notes

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