Water → HCID 15239004, compound

HRID 1195088Notes

Reaction equation

HRID 1195088 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:18])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH:8]=[CH:7]2.[F:19][C:20]([F:32])([F:31])[C:21]1[CH:22]=[C:23]([Sn](C)(C)C)[CH:24]=[CH:25][CH:26]=1.C(OCC)(=O)C.O>C1(C)C=CC=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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].CCCCCC.C(OCC)(=O)C>[CH3:18][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([C:20]([F:32])([F:31])[F:19])[CH:26]=3)[CH:3]=1)[N:10]=[C:9]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH:8]=[CH:7]2

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 13139018Trimethyl[3-(trifluoromethyl)phenyl]stannaneHCID 15239003HCID 15239003, compound

Product 1

HCID 15239004HCID 15239004, compoundYield 29.3%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 1.5 g (6.2 mmol) of 8-bromo-6-methyl-2-(2,2,2-trifluoroethoxy)quinoline, 2.3 g of crude 3-(trifluoromethyl)phenyltrimethylstannane (Example 1), and 0.2 g of tetrakis(triphenylphosphine)palladium(O) was heated in 30 ml of toluene at reflux with stirring for 3 hours. Ethyl acetate (200 ml) and excess water was added. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo to give an oil. Silica gel column chromatography (20:1 followed by 10:1 hexane/ethyl acetate) afforded 0.7 g of product, isolated as an oil. NMR(CDCl3): ppm 2.55 (s, 3H), 4.71 (q, 2H), 7.15 (d, 1H), 7.5-8.15 (m, 7H).

Workup

  1. temperatureat reflux
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customto give an oil

Sources & evidence

ORD record
ord-eb710d48b4364b57bab6c8f95a4d0e2b
Source dataset
uspto-grants-1992_05
Patent number
US05110347

Reaction notes

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