Piperidine → HCID 11610989, compound

HRID 2104163Notes

Reaction equation

HRID 2104163 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:54]1[CH:55]=[C:56]2[C:61](=[CH:62][CH:63]=1)[N:60]=[C:59]([CH3:64])[C:58]([C:65](=[O:70])[C:66]([F:69])([F:68])[F:67])=[C:57]2[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1.[NH:77]1[CH2:82][CH2:81][CH2:80][CH2:79][CH2:78]1>CCCCCCC.C(O)(C)(C)C.O1CCOCC1>[F:67][C:66]([F:69])([F:68])[C:65]([C:58]1[C:59]([CH3:64])=[N:60][C:61]2[C:56]([C:57]=1[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)=[CH:55][C:54]([N:77]1[CH2:82][CH2:81][CH2:80][CH2:79][CH2:78]1)=[CH:63][CH:62]=2)=[O:70]

Participants

8

Reactant 4

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 11710932HCID 11710932, compound

Product 1

HCID 11610989HCID 11610989, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 6386tert-ButanolSolventHCID 8900HeptaneSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared according to the general procedure of method B. Following a methodology developed by J. P. Wolfe and S. L. Buchwald (J. Org. Chem. 2000, 65, 1144-1157) a screw-topped pressure-resistant glass vial (50 mL) equipped with a magnetic stirring bar was flushed with a stream of argon and charged with tris(dibenzylideneacetone)dipalladium chloroform complex (0.01 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.02 mmol), dioxane (7.5 mL) and tert.-butanol (7.5 mL) and then stirred for 1 min before adding cesium carbonate (1.4 mmol), 1-(6-Bromo-2-methyl-4-phenyl-quinolin-3-yl)-2,2,2-trifluoro-ethanone [example 3] (1 mmol), and piperidine (1.2 mmol). The glass vial was covered with a pressure-resistant seal, firmly locked by a screw-cap and heated with stirring in an oil bath at 120° C. during 2 h. The glass vial was cooled in ice before opening, the reaction mixture was diluted with heptane (5 mL) and filtered through a plug of Dicalite filter-aid and rinsed with heptane. The filtrate was evaporated and the residue purified by chromatography on silica gel in heptane/ethyl acetate (4:1). Yield: 74%; MS: m/z=399 (M+H).

Workup

  1. customBuchwald (J. Org. Chem. 2000, 65, 1144-1157) a screw-topped pressure-resistant glass vial (50 mL) equipped with a magnetic stirring bar
  2. customwas flushed with a stream of argon
  3. customa screw-cap
  4. temperatureheated
  5. stirringwith stirring in an oil bath at 120° C. during 2 h
  6. temperatureThe glass vial was cooled in ice before opening
  7. filtrationfiltered through a plug of Dicalite
  8. filtrationfilter-aid
  9. washrinsed with heptane
  10. customThe filtrate was evaporated
  11. customthe residue purified by chromatography on silica gel in heptane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-56ae4d730dc14e4eb1cac598e150f89d
Source dataset
uspto-grants-2009_08
Patent number
US07576217B2

Reaction notes

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