HCID 57968783, compound → 6-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-2-[(2-hydroxy-ethyl)-methyl-amino]-nicotinonitrile

HRID 1471563Notes

Reaction equation

HRID 1471563 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9](Cl)[N:8]=2)=[CH:4][C:3]=1[CH:18]1[O:22][CH2:21][CH2:20][O:19]1.BrC1C=CC(OC2N=C(Cl)C=CC=2C#N)=CC=1C1OCCO1.C([O:52][CH2:53][CH2:54][NH:55][C:56]1N=C(OC2C=CC(Br)=C(C=O)C=2)C=CC=1C#N)C1C=CC=CC=1>C(#N)C>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([N:55]([CH2:54][CH2:53][OH:52])[CH3:56])[N:8]=2)=[CH:4][C:3]=1[CH:18]1[O:22][CH2:21][CH2:20][O:19]1

Participants

5

Reactant 3

HCID 57968783HCID 57968783, compoundHCID 86636428HCID 86636428, compoundHCID 866364442-(2-Benzyloxy-ethylamino)-6-(4-bromo-3-formyl-phenoxy)-nicotinonitrile

Product 1

HCID 674392076-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-2-[(2-hydroxy-ethyl)-methyl-amino]-nicotinonitrileYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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 in vacuo. Purification was accomplished by silica gel chromatography, eluting with 10%-80% EtOAc/hexanes gradient, affording 400 mg (36% yield) of the title compound.

Workup

  1. customAfter the reaction
  2. customall volatile components were evaporated in vacuo
  3. customPurification
  4. washeluting with 10%-80% EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-522b696352a542fc849078aa990168ee
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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