Methanol → methylphosphonothioic acid O-[3-(1H-indol-2-yl)-1H-indazol-5-yl]ester O-methyl ester

HRID 1726108Notes

Reaction equation

HRID 1726108 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=C[C:26]([O:29][P:30]([CH3:42])(=[S:41])OC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=O.N12CCCN=C1CCCCC2.CO>ClCCl>[CH3:26][O:29][P:30]([CH3:42])(=[S:41])[O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

6

Reactant 4

HCID 887MethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 11416910methylphosphonothioic acid O,O-bis-(4-nitrophenyl)esterHCID 1360559793-(1H-indol-2-yl)-1H-indazol-5-ol2×

Product 1

HCID 136355257methylphosphonothioic acid O-[3-(1H-indol-2-yl)-1H-indazol-5-yl]ester O-methyl esterYield 16.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

The compound methylphosphonothioic acid O-[3-(1H-indol-2-yl)-1H-indazol-5-yl]ester O-methyl ester is prepared according to procedure F using 200 mg of 3-(1H-indol-2-yl)-H-indazole-5-ol (intermediate B) in solution with 284 mg of methylphosphonothioic acid O,O—bis-(4-nitrophenyl)ester in 6 ml of dichloromethane (stabilized with amylene), to which 120 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in solution in 1 ml of dichloromethane are added. After stirring at ambient temperature for 4 h 30 min, 325 μl of methanol and 120 μl of DBU in solution in 1 ml of dichloromethane are added. The mixture is left at ambient temperature overnight and the solvent is then evaporated off and the crude is purified by flash chromatography on 35-70 μm silica, eluent: cyclohexane/ethyl acetate 90/10 to 50/50. The fractions obtained are concentrated and purified by preparative LC/MS to obtain 47.7 mg of methylphosphonothioic acid O-[3-(1H-indol-2-yl)-1H-indazol-5-yl]ester O-methyl ester.

Workup

  1. customThe compound methylphosphonothioic acid O-[3-(1H-indol-2-yl)-1H-indazol-5-yl]ester O-methyl ester is prepared
  2. waitThe mixture is left at ambient temperature overnight
  3. customthe solvent is then evaporated off
  4. customthe crude is purified by flash chromatography on 35-70 μm silica, eluent
  5. customThe fractions obtained
  6. concentrationare concentrated
  7. custompurified by preparative LC/MS

Sources & evidence

ORD record
ord-40db2c9490c14b8d8ed963263753ec1a
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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