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

HRID 605213

반응식

HRID 605213 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c8749a8574984cab809137d791ee5269
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

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