4-Chlorophenol → HCID 117816809, compound

HRID 1497389Notes

Reaction equation

HRID 1497389 reaction equation
CS([O:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]([C:13]2[CH:21]=[CH:20][C:19]3[C:15](=[C:16]([CH3:23])[N:17]([CH3:22])[N:18]=3)[CH:14]=2)[C:9](=[O:24])[CH:8]=1)(=O)=O.[Cl:25][C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][N:10]([C:13]3[CH:21]=[CH:20][C:19]4[C:15](=[C:16]([CH3:23])[N:17]([CH3:22])[N:18]=4)[CH:14]=3)[C:9](=[O:24])[CH:8]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 117798604HCID 117798604, compound

Product 1

HCID 117816809HCID 117816809, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [1-(2,3-dimethyl-2H-indazol-5-yl)-2-oxo-1,2-dihydropyridin-4-yl]methyl methanesulfonate (140 mg) and 4-chlorophenol (77 mg) in N,N-dimethylformamide (5 ml) was added potassium carbonate (120 mg) at room temperature, and the mixture was stirred at 80° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (dichloromethane/methanol). The obtained residue was purified by HPLC to give the title compound (20 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (dichloromethane/methanol)
  3. customThe obtained residue was purified by HPLC

Sources & evidence

ORD record
ord-eb5628d154ce4586aa39513f0127a28b
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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