Ethanol → phenylphosphonic acid 1H-indazol-5-yl ester methyl ester
Reaction equation
[N+](C1C=C[C:7]([O:10][P:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])[O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18](C(=O)C)[N:17]=[CH:16]3)=CC=1)([O-])=O.C(O)C.CO.N12CCCN=C1CCCCC2>ClCCl>[CH3:7][O:10][P:11]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:25])[O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[CH:16]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A solution of 2.4 g of phenylphosphonic acid 1-acetyl-1H-indazol-5-yl ester 4-nitrophenyl ester in 30 ml of dichloromethane stabilized with ethanol is stirred at 20° C. A solution of 3.78 ml of methanol and of 836 mg of 1,8-diazabicyclo[5.4.0]undec-7-ene in 30 ml of dichloromethane is added thereto. The reaction is continued at this temperature overnight. The reaction mixture is evaporated under reduced pressure and the crude compound thus obtained is then purified by chromatography on silica (AIT BP-SUP 20-40 μm, eluent 90/10 dichloromethane/methanol). The fractions containing the expected compound are combined and evaporated under reduced pressure. 980 mg of phenylphosphonic acid 1H-indazol-5-yl ester methyl ester are isolated and characterized.
Workup
- customis continued at this temperature overnight
- customThe reaction mixture is evaporated under reduced pressure
- customthe crude compound thus obtained
- customis then purified by chromatography on silica (AIT BP-SUP 20-40 μm, eluent 90/10 dichloromethane/methanol)
- additionThe fractions containing the expected compound
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-c11e89cb09dc483b98758da4e5ca38e5
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491710B2
Reaction notes
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