Methanol → methylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl ester

HRID 1726068Notes

Reaction equation

HRID 1726068 reaction equation
[N+](C1C=C[C:7]([O:10][P:11]([CH3:23])(=[O:22])[O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=CC=1)([O-])=O.[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1[C:33]1C2C(=CC=C(O)C=2)N[N:34]=1.N12CCCN=C1CCCCC2.CO>ClCCl>[CH3:7][O:10][P:11]([CH3:23])(=[O:22])[O:12][C:13]1[CH:14]=[C:15]2[C:16](=[CH:17][CH:18]=1)[NH:19][N:34]=[C:33]2[C:25]1[NH:24][C:32]2[C:27]([CH:26]=1)=[CH:28][CH:29]=[CH:30][CH:31]=2

Participants

6

Reactant 4

HCID 887MethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 98876Bis(4-nitrophenyl) methylphosphonateHCID 1360559793-(1H-indol-2-yl)-1H-indazol-5-ol

Product 1

HCID 136055995methylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl esterYield 26.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Methylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl ester is prepared according to procedure F using 150 mg of methylphosphonic acid bis-(4-nitrophenyl) ester, 4 ml of dichloromethane, 100 mg of 3-(1H-indol-2-yl)-1H-indazol-5-ol, 67 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene and 4 ml of dichloromethane. After stirring for 3 hours, a solution of 100 μl of methanol in 2 ml of dichloromethane is added dropwise. The reaction medium is stirred for approximately 16 hours and then concentrated to dryness under reduced pressure. The oil obtained is purified on a 5 g Interchim flash cartridge of silica with a particle size of 15-35 μ. Eluent: 30% of ethyl acetate in cyclohexane, then with 80% of ethyl acetate in methanol. The solvents are evaporated off under reduced pressure and the product obtained is crystallized from ethyl acetate. 36 mg of methylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl ester are obtained in the form of white crystals.

Workup

  1. customMethylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl ester is prepared
  2. stirringThe reaction medium is stirred for approximately 16 hours
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe oil obtained
  5. customis purified on a 5 g Interchim flash cartridge of silica with a particle size of 15-35 μ
  6. customThe solvents are evaporated off under reduced pressure
  7. customthe product obtained
  8. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-4a35f9c9de6f499e83a78b5cb3d971cf
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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