Cesium carbonate → HCID 15956116, compound

HRID 1474021Notes

Reaction equation

HRID 1474021 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[OH:15].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[O:15][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 68488969HCID 68488969, compound

Product 1

HCID 15956116HCID 15956116, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation of 2-R-5-(heteroaryl-2-ylamino)phenol, 2-chloro-5-(pyridin-2-ylamino)phenol (34 mg, 0.15 mmol) and Cs2CO3 (51 mg, 0.16 mmol) in acetone (1.5 mL) was treated with 4-bromo-2-methyl-2-butene (0.017 mL, 0.15 mmol) at room temperature. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 8/2) in 74% yield (32 mg).

Sources & evidence

ORD record
ord-9923fd83dfb14337972e7f36b28f7e2e
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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