Triethylamine → HCID 23206554, compound

HRID 1289431Notes

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[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=2)[N:20]=[CH:19][CH:18]=1>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[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:30])([F:28])[F:29])[CH:25]=2)[N:20]=[CH:19][CH:18]=1)(=[O:15])[O:12][CH2:13][CH3:14])[CH3:9]

Participants

Conditions

Temperature: 90 °C

Procedure

1.73 g of tetrakis-(triphenylphosphine)-palladium(O) in 20 ml of toluene is mixed with 4.6 ml of triethylamine, 4.3 ml of diethylphosphite and 8.28 g of 4-bromo-6-trifluoromethyl-quinoline and stirred for three hours at 90° C. Another 0.17 g of tetrakis-(triphenylphosphine)-palladium(O) and 0.4 ml of triethylamine and diethylphosphite each are added and stirred for one hour at 90° C. After cooling, it is diluted with ether, suctioned off, washed with ether and the filtrate is concentrated by evaporation. The product is purified by column chromatography. 8.33 g of 6-trifluoromethyl-quinoline-4-phosphonic acid diethyl ester is obtained as colorless oil.

Workup

stirringstirred for one hour at 90° C
temperatureAfter cooling
washwashed with ether
concentrationthe filtrate is concentrated by evaporation
customThe product is purified by column chromatography

Sources & evidence

ORD record: ord-e35a5e7d84824413b4e4ee5c2567fee7
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750526

Reaction notes

Loading…