Sodium Chloride → phenylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl ester

HRID 1726065Notes

Reaction equation

HRID 1726065 reaction equation
[N+](C1C=C[C:7]([O:10][P:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=O)[O:12]C2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=O.[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]1[C:38]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44]([OH:47])[CH:45]=2)[NH:40][N:39]=1.N12CCCN=C1CCCCC2.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>ClCCl>[CH3:7][O:10][P:11]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:12])[O:47][C:44]1[CH:45]=[C:46]2[C:41](=[CH:42][CH:43]=1)[NH:40][N:39]=[C:38]2[C:30]1[NH:29][C:37]2[C:32]([CH:31]=1)=[CH:33][CH:34]=[CH:35][CH:36]=2

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 170133Bis(4-nitrophenyl) P-phenylphosphonateHCID 516892Sodium BicarbonateHCID 1360559793-(1H-indol-2-yl)-1H-indazol-5-ol

Product 1

HCID 136055973phenylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl esterYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Phenylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl ester is prepared according to procedure F using 230 mg of phenyl-phosphonic acid bis-(4-nitrophenyl) ester in solution in 4 ml of dichloromethane to which is added a solution of 120 mg of 3-(1H-indol-2-yl)-1H-indazol-5-ol and 72 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene in 4 ml of dichloromethane. After stirring for 2 hours at ambient temperature, the medium is treated with 4 times 50 ml of a saturated sodium bicarbonate solution, and then with 2×50 ml of a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and then concentrated to dryness to obtain 200 mg of crude phenylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl ester.

Workup

  1. customPhenylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl ester is prepared
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0f206f75f0264c24a797d5131fdc5427
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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