Cesium carbonate → HCID 15956115, compound

HRID 1474020Notes

Reaction equation

HRID 1474020 reaction equation
[CH3:1][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>[CH3:1][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 68489605HCID 68489605, compound

Product 1

HCID 15956115HCID 15956115, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation of 2-R-5-(heteroaryl-2-ylamino)phenol, 2-methyl-5-(pyridin-2-ylamino)phenol (67 mg, 0.33 mmol) and Cs2CO3 (113 mg, 0.35 mmol) in acetone (3.3 mL) was treated with 4-bromo-2-methyl-2-butene (0.038 mL, 0.33 mmol) at room temperature. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 8/2) in 48% yield (43 mg).

Sources & evidence

ORD record
ord-11230bc2c0a24bda84c86bd65b377d40
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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