Ammonia → 4-[(4-chlorobenzyl)oxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497357ノート

反応式

HRID 1497357 の反応式
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[C:5]([CH3:12])[N:6]([CH3:11])[N:7]=2)[CH:3]=1.[Cl:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][NH:23][C:22](=[O:26])[CH:21]=2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC.N>CS(C)=O.[Cu]I>[Cl:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][N:23]([C:2]3[CH:10]=[CH:9][C:8]4[C:4](=[C:5]([CH3:12])[N:6]([CH3:11])[N:7]=4)[CH:3]=3)[C:22](=[O:26])[CH:21]=2)=[CH:16][CH:15]=1

参加物

8

反応物 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 114995675-bromo-2,3-dimethyl-2H-indazoleHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-one

生成物 1

HCID 865829744-[(4-chlorobenzyl)oxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one収率 31%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
150 °C

実験手順

A suspension of 5-bromo-2,3-dimethyl-2H-indazole (287 mg), 4-[(4-chlorobenzyl)oxy]pyridin-2(1H)-one (300 mg), potassium carbonate (528 m g), copper(I) iodide (242 mg) and N,N′-dimethylethylenediamine (112 mg) in DMSO (10 ml) was stirred at 150° C. for 3 hr. The reaction mixture was cooled to room temperature, added to 28% aqueous ammonia, and extracted with a 1:1 mixed solvent of ethyl acetate and tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (150 mg).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with a 1:1 mixed solvent of ethyl acetate and tetrahydrofuran
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol)

出典と根拠

ORDレコード
ord-4be5abcf7a1e46e5822172de251cdf8e
出典データセット
uspto-grants-2015_12
特許番号
US09199963B2

反応ノート

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