Methanol → HCID 136055990, compound

HRID 1726109Notes

Reaction equation

HRID 1726109 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=C[C:24]=1[O:29][P:30]([CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)(=O)[O:31]C1C=CC=CC=1[N+]([O-])=O)([O-])=O.N12CCCN=C1CCCCC2.CO>ClCCl>[CH3:24][O:29][P:30]([CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)(=[O:31])[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-eneHCID 86598880HCID 86598880, compoundHCID 1360559793-(1H-indol-2-yl)-1H-indazol-5-ol2×

Product 1

HCID 136055990HCID 136055990, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

The compound cyclohexylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl ester is prepared according to procedure F using 200 mg of 3-(1H-indol-2-yl)-H-indazol-5-ol (intermediate B) in solution with 325 mg of cyclohexylphosphonic acid bis(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 hours 30 minutes, 325 μl of methanol 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 64.5 mg of cyclohexylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester methyl ester.

Workup

  1. customThe compound cyclohexylphosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester 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-cdc058d036834f99971e943855a9bf95
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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