Potassium Carbonate → Tert-butyl {4-methyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate

HRID 1800501ノート

反応式

HRID 1800501 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[OH:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:15]=[CH:16][C:17]=1[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:18][C:17]1[CH:16]=[CH:15][C:14]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[CH:13][C:12]=1[O:11][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 44668374tert-butyl N-(3-hydroxy-4-methylphenyl)carbamate

生成物 1

HCID 86646009Tert-butyl {4-methyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate収率 92%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a solution of 2-chloro-5-nitropyridine (15.0 g, 94.5 mmol) and tert-butyl (3-hydroxy-4-methylphenyl)carbamate (20.0 g, 90.0 mmol) in N,N-dimethylformamide (200 mL) was added potassium carbonate (18.6 g, 135 mmol), and the mixture was stirred at 70° C. for 18 hr. The reaction mixture was cooled to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Water (400 mL) was added to the obtained residue, and the mixture was extracted with ethyl acetate (400 mL×2). The combined organic layer was washed with saturated brine (300 mL×2), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate), and the obtained solution was concentrated under reduced pressure. The residue was triturated with hexane to give the title compound (28.6 g, 92%) as a pale-yellow solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater (400 mL) was added to the obtained residue
  5. extractionthe mixture was extracted with ethyl acetate (400 mL×2)
  6. washThe combined organic layer was washed with saturated brine (300 mL×2)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate)
  11. concentrationthe obtained solution was concentrated under reduced pressure
  12. customThe residue was triturated with hexane

出典と根拠

ORDレコード
ord-e2a642f07ff14b37939311d23f3f2b8b
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

反応ノート

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