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

HRID 1726054Notes

Reaction equation

HRID 1726054 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][P:11]([CH3:19])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1)([O-])=O.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[C:29]1C2C(=CC=C(O)C=2)N[N:30]=1.N12CCCN=C1CCCCC2>ClCCl>[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[C:29]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:10][P:11]([CH3:19])([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[CH:8]=2)[NH:1][N:30]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1147964-Nitrophenyl P-methyl-P-phenylphosphinateHCID 1360559793-(1H-indol-2-yl)-1H-indazol-5-ol

Product 1

HCID 136055967methylphenylphosphinic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 497 mg of 50%-pure methylphenylphosphinic acid 4-nitrophenyl ester in 8 ml of dichloromethane is stirred at ambient temperature. A suspension of 403 mg of 3-(1H-indol-2-yl)-1H-indazol-5-ol and 268 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene in 12 ml of dichloromethane is added dropwise. The reaction medium is stirred at ambient temperature overnight and then evaporated to dryness under reduced pressure in a rotary evaporator. The reaction crude is purified by flash chromatography on a cartridge of 50 g of silica 15-35 μm. 300 mg of methylphenylphosphinic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester are collected and recrystallized from ethyl acetate to obtain 220 mg of methylphenylphosphinic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester.

Workup

  1. additionis added dropwise
  2. customevaporated to dryness under reduced pressure in a rotary evaporator
  3. customThe reaction crude
  4. customis purified by flash chromatography on a cartridge of 50 g of silica 15-35 μm
  5. custom300 mg of methylphenylphosphinic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester are collected
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c60ecef54d794526965a742e90793216
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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