Cesium carbonate → 2-(3-Methylbut-2-enoxy)-4-(2-pyridylamino)benzonitrile

HRID 1474022Notes

Reaction equation

HRID 1474022 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][C:4]=1[OH:16])#[N:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]>CC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][C:4]=1[O:16][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])#[N:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 684879352-Cyano-5-(pyridin-2-ylamino)phenol

Product 1

HCID 159561172-(3-Methylbut-2-enoxy)-4-(2-pyridylamino)benzonitrileYield 38%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation of 2-R-5-(heteroaryl-2-ylamino)phenol, 2-cyano-5-(pyridin-2-ylamino)phenol (2 mg, 0.01 mmol) and Cs2CO3 (3 mg, 0.01 mmol) in acetone (1.5 mL) was treated with 4-bromo-2-methyl-2-butene (1.1 μL, 0.01 mmol) at room temperature. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 7/3) in 38% yield (1 mg).

Sources & evidence

ORD record
ord-27519860195a4414aadfca06f0f6b753
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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