1,8-Diazabicyclo(5.4.0)undec-7-ene → dimethylphosphinic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester

HRID 1726083Notes

Reaction equation

HRID 1726083 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:19])[CH:17]=2)[NH:12][N:11]=1.[N+](C1C=CC([O:29][P:30]([CH3:33])([CH3:32])=O)=CC=1)([O-])=O.N12CCCN=C1CCCCC2>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][P:30]([CH3:33])([CH3:32])=[O:29])[CH:17]=2)[NH:12][N:11]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 166793Phosphinic acid, dimethyl-, p-nitrophenyl esterHCID 1360559793-(1H-indol-2-yl)-1H-indazol-5-ol2×

Product 1

HCID 136055994dimethylphosphinic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl esterYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The dimethylphosphinic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester compound is prepared according to procedure F using 230 mg of 3-(1H-indol-2-yl)-1H-indazol-5-ol (intermediate B) in solution with 245 mg of dimethylphosphinic acid 4-nitrophenyl ester in 5 ml of dichloromethane (stabilized with amylene) to which 170 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in solution in 2 ml of dichloromethane are added. After stirring for 24 h at ambient temperature, the solvent is evaporated off and the crude is purified by preparative LC/MS. The crystals obtained after concentration of the fractions are washed with ethyl acetate and then with isopropyl ether. 129 mg of expected product are collected. Yield=43%.

Workup

  1. additionare added
  2. customthe solvent is evaporated off
  3. customthe crude is purified by preparative LC/MS
  4. customThe crystals obtained after concentration of the fractions
  5. washare washed with ethyl acetate
  6. custom129 mg of expected product are collected

Sources & evidence

ORD record
ord-316e1ee481684e4cba0966f68fcfe0d0
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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