Triethylamine → HCID 178502975, compound

HRID 1726073Notes

Reaction equation

HRID 1726073 reaction equation
[P:1]([O-:6])([O:4][CH3:5])[O:2][CH3:3].C(N(CC)CC)C.[CH:14](/[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28](OS(C(F)(F)F)(=O)=O)[CH:29]=2)[NH:24][N:23]=1)=[CH:15]\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:3][O:2][P:1]([C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[NH:24][N:23]=[C:22]2/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:6])[O:4][CH3:5]

Participants

6

Reactant 3

HCID 8471Triethylamine3×HCID 21884954Dimethylphosphite3×HCID 57562448HCID 57562448, compound

Product 1

HCID 178502975HCID 178502975, compoundYield 6.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst3×HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

40.7 μl (1.09 eq; 0.444 mmol) of dimethyl phosphite, 61.9 μl (1.09 eq; 0.444 mmol) of triethylamine and 18.8 mg (0.04 eq; 0.016 mmol) of tetrakis(triphenylphosphine)palladium(0) are stirred under an argon atmosphere for 15 minutes. 150 mg (1 eq; 0.407 mmol) of trifluoromethanesulfonic acid 3-((E)-styryl)-1H-indazol-5-yl ester in solution in 5 ml of dimethylformamide are added. The medium is heated at 85° C. overnight. 41 μl of dimethylphosphite, 62 μl of triethylamine and 20 mg of tetrakis(triphenylphosphine)palladium(0) are added to the medium, which is heated for a further two hours. 100 μl of dimethylphosphite, 100 μl of triethylamine and 30 mg of tetrakis(triphenylphosphine)palladium(0) are then added to the medium, which is heated overnight at 105° C. After filtration of the catalyst through filter paper, the solvent is evaporated off under reduced pressure in a rotary evaporator. The reaction crude is purified by LC/MS to obtain 8.6 mg of [3-((E)-styryl)-1H-indazol-5-yl]phosphonic acid dimethyl ester, along with 27.2 mg of [3-((E)-styryl)-1H-indazol-5-yl]phosphonic acid monomethyl ester (Example 13).

Workup

  1. temperatureis heated for a further two hours
  2. temperatureis heated overnight at 105° C
  3. filtrationAfter filtration of the catalyst
  4. filtrationthrough filter paper
  5. customthe solvent is evaporated off under reduced pressure in a rotary evaporator
  6. customThe reaction crude
  7. customis purified by LC/MS

Sources & evidence

ORD record
ord-5d66c59a2e1949019742031a1ff6fa74
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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