Triethylamine → HCID 23206536, compound

HRID 1289429Notes

Reaction equation

HRID 1289429 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][P:11]([O-:15])[O:12][CH2:13][CH3:14])[CH3:9].Br[C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][C:23]([C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=2>C1(C)C=CC=CC=1.CCOCC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH2:8]([O:10][P:11]([C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][C:23]([C:27]([F:29])([F:30])[F:28])=[CH:22][CH:21]=2)(=[O:15])[O:12][CH2:13][CH3:14])[CH3:9]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 18921566HCID 18921566, compound

Product 1

HCID 23206536HCID 23206536, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

1.44 g of tetrakis-(triphenylphosphine)-palladium(O) are introduced in 16 ml of toluene, 3.8 ml of triethylamine and 3.6 ml of diethylphosphite at room temperature under nitrogen and mixed with 6.90 g of 3-bromo-6-trifluoromethyl-quinoline. It is stirred for two hours at 90° C. bath temperature. The mixture is diluted with ether, suctioned off and the filtrate is concentrated by evaporation. After column chromatography, 8.3 g of 6-trifluoromethyl-quinoline-3-phosphonic acid diethyl ester of melting point 69° C. is obtained.

Workup

  1. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-eac2a190f7824a27b7782a8ee081630f
Source dataset
uspto-grants-1998_05
Patent number
US05750526

Reaction notes

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