正亚磷酸 → 5-Amino-1-(2-bromo-5-nitrophenyl)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide

HRID 64332

反应方程式

HRID 64332 反应方程式
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=2[Br:16])[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[C:3]=1[C:30]#[N:31].P(O)(O)[OH:33]>>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=2[Br:16])[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[C:3]=1[C:30]([NH2:31])=[O:33]

参与物

3

反应物 2

HCID 107909正亚磷酸HCID 1176682135-amino-1-(2-bromo-5-nitrophenyl)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile

产物 1

HCID 1176682335-Amino-1-(2-bromo-5-nitrophenyl)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide

反应条件

温度
100 °C

实验过程

A mixture of 5-amino-1-(2-bromo-5-nitrophenyl)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile (137 mg, 0.287 mmol) in phosphorous acid (85 wt. % in H2O, 10 mL) was stirred at 100° C. for 1 hr, until TLC and LCMS analysis showed that most of starting material was consumed. The reaction was cooled to room temperature and partitioned between water (40 mL) and EA (40 mL). Organic layer was separated from aqueous layer. The aqueous phase was then extracted with EA (20 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4 and concentrated to get the crude product (149 mg) which was used in next step without further purification. MS (ESI) m/e [M+1]+494, 496.

后处理

  1. customwas consumed
  2. temperatureThe reaction was cooled to room temperature
  3. custompartitioned between water (40 mL) and EA (40 mL)
  4. customOrganic layer was separated from aqueous layer
  5. extractionThe aqueous phase was then extracted with EA (20 mL)
  6. washThe combined organic layers were washed with brine (50 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

来源与证据

ORD记录
ord-c4bb597513e8498b81f19dd0b55f5f5b
来源数据集
uspto-grants-2016_09
专利号
US09447106B2

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