Dichloromethane → phenylphosphonic acid 1H-indazol-5-yl ester methyl ester

HRID 1726070Notes

Reaction equation

HRID 1726070 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.ClCCl.N12CCCN=C1CCCCC2>CO>[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]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57562494phenylphosphonic acid 1-acetyl-1H-indazol-5-yl ester 4-nitrophenyl ester

Product 1

HCID 57562461phenylphosphonic acid 1H-indazol-5-yl ester methyl esterYield 10.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenylphosphonic acid 1H-indazol-5-yl ester methyl ester is prepared according to procedure F using 219 mg of phenyl-phosphonic acid 1-acetyl-1H-indazol-5-yl ester 4-nitrophenyl ester, 5 ml of dichloromethane, 74.8 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene and 202 μl of methanol. The crude is purified by flash chromatography on silica with a particle size of 35-70 μm. Eluent: cyclohexane then 80:20 cyclohexane/ethyl acetate to obtain 15 mg of phenylphosphonic acid 1H-indazol-5-yl ester methyl ester in the form of a colorless oil.

Workup

  1. customPhenylphosphonic acid 1H-indazol-5-yl ester methyl ester is prepared
  2. customThe crude is purified by flash chromatography on silica with a particle size of 35-70 μm

Sources & evidence

ORD record
ord-6d213b39f935484e95d9ca8ce41096a2
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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