Triethylamine → HCID 178476928, compound

HRID 1726075Notes

Reaction equation

HRID 1726075 reaction equation
[CH:1](/[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:16]=2)[NH:11][N:10]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:26]([O:28][P:29]([O-:33])[O:30][CH2:31][CH3:32])[CH3:27].C(N(CC)CC)C>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>[CH2:26]([O:28][P:29]([C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2/[CH:1]=[CH:2]/[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:33])[O:30][CH2:31][CH3:32])[CH3:27].[CH2:26]([O:28][P:29]([C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2/[CH:1]=[CH:2]/[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:30])[OH:33])[CH3:27]

Participants

8

Reactant 3

HCID 8471Triethylamine4×HCID 3780918Diethylphosphite4×HCID 57562448HCID 57562448, compound

Product 2

HCID 178476928HCID 178476928, compoundHCID 178476953HCID 178476953, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 178418397HCID 178418397, compoundCatalyst3×HCID 6228DimethylformamideSolvent

Procedure

Procedure H is followed, introducing 70 mg (1 eq; 0.190 mmol) of trifluoromethanesulfonic acid 3-((E)-styryl)-1H-indazol-5-yl ester in solution in 3 ml of dimethylformamide, 26.7 μl (1.09 eq; 0.207 mmol) of diethylphosphite, 8.9 mg (0.04 eq-0.0076 mmol) of tetrakis(triphenylphosphine)palladium(0) and 28.8 μl (1.09 eq; 0.207 mmol) of triethylamine. The additions made are successively 27 μl of diethylphosphite, 29 μl of triethylamine, 10 mg of tetrakis(triphenylphosphine)palladium(0), then 50 μl of diethylphosphite, 50 μl of triethylamine, 20 mg of tetrakis(triphenylphosphine)palladium(0) and, finally, 27 μl of diethylphosphite, 29 μl of triethylamine and 9 mg of tetrakis(triphenylphosphine) palladium(0). 22 mg of [3-((E)-styryl)-1H-indazol-5-yl]phosphonic acid diethyl ester are isolated, along with 8.7 mg of [3-((E)-styryl)-1H-indazol-5-yl]phosphonic acid monoethyl ester.

Sources & evidence

ORD record
ord-7080fc027080459ca05c21e948863195
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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