Potassium Carbonate → {4-[4-(5-Chloro-pyridin-2-ylcarbamoyl)-2-nitro-phenoxy]-phenyl}-carbamic acid tert-butyl ester

HRID 605213ノート

反応式

HRID 605213 の反応式
Cl[C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)=[O:7])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[C:21]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:24]([O:23][C:21](=[O:22])[NH:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][C:2]2[CH:17]=[CH:16][C:5]([C:6](=[O:7])[NH:8][C:9]3[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=3)=[CH:4][C:3]=2[N+:18]([O-:20])=[O:19])=[CH:33][CH:34]=1)([CH3:27])([CH3:25])[CH3:26]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 6930954-chloro-N-(5-chloropyridin-2-yl)-3-nitrobenzamideHCID 2756771N-Boc-4-hydroxyaniline

生成物 1

HCID 67040773{4-[4-(5-Chloro-pyridin-2-ylcarbamoyl)-2-nitro-phenoxy]-phenyl}-carbamic acid tert-butyl ester収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A solution of the product of Example 199A (300 mg, 0.9612 mmol) in anhydrous N,N-dimethylformamide (5 mL) was treated with N-Boc-4-hydroxyaniline (201 mg, 0.9612 mmol) and potassium carbonate (266 mg, 1.922 mmol) at room temperature, then heated at 80° C. under a nitrogen atmosphere for 5 hours. The reaction was cooled to room temperature and the solvent removed by rotary evaporation in vacuo. The residue was taken up in ethyl acetate (100 mL) and washed with water (4×50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation in vacuo. Trituration with 5% ethyl acetate gave the title compound (284 mg, 61%).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. customthe solvent removed by rotary evaporation in vacuo
  3. washwashed with water (4×50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation in vacuo

出典と根拠

ORDレコード
ord-c8749a8574984cab809137d791ee5269
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

反応ノート

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