Imidazole → methylphenylphosphinic acid 3-((E)-styryl)-1H-indazol-5-yl ester

HRID 1726052Notes

Reaction equation

HRID 1726052 reaction equation
[CH:1]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[NH:11][N:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CN=C1.[CH3:24][P:25](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26].O>ClCCl>[CH:1](/[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][P:25]([CH3:24])([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])[CH:16]=2)[NH:11][N:10]=1)=[CH:2]\[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 795Imidazole3×HCID 962WaterHCID 21983Methyl(phenyl)phosphinoyl chloride3×HCID 688387233-styryl-1H-indazol-5-ol

Product 1

HCID 11428770methylphenylphosphinic acid 3-((E)-styryl)-1H-indazol-5-yl esterYield 28.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 20 mg of 3-styryl-1H-indazol-5-ol, 5.76 mg of imidazole and 20.7 mg of methylphenylphosphinic chloride in 5 ml of dichloromethane is stirred at ambient temperature. After stirring for approximately one hour, 5.76 mg of imidazole and 20.7 mg of methylphenylphosphinic chloride are added. The suspension is stirred at ambient temperature for approximately 18 hours. 10 mg of imidazole and 70 mg of methylphenylphosphinic chloride are added. After 30 hours at ambient temperature, the reaction medium is treated with 10 ml of distilled water. The aqueous phase is extracted with 2×10 ml of dichloromethane. The organic phase is dried over magnesium sulfate and concentrated under reduced pressure in a rotary evaporator. The reaction crude is purified by preparative LC/MS to obtain 9.1 mg of methylphenylphosphinic acid 3-((E)-styryl)-1H-indazol-5-yl ester.

Workup

  1. stirringThe suspension is stirred at ambient temperature for approximately 18 hours
  2. waitAfter 30 hours at ambient temperature
  3. extractionThe aqueous phase is extracted with 2×10 ml of dichloromethane
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure in a rotary evaporator
  6. customThe reaction crude
  7. customis purified by preparative LC/MS

Sources & evidence

ORD record
ord-619dbf0ab4d84c8fac3c44929f522b7f
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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