Water → HCID 15239004, compound

HRID 2395933Notes

Reaction equation

HRID 2395933 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 atreflux 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. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customto give an oil

Sources & evidence

ORD record
ord-51bdbb4010644b33957dfa25c5fae20f
Source dataset
uspto-grants-1996_02
Patent number
US05491126

Reaction notes

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