Cesium carbonate → HCID 58368476, compound

HRID 1192544Notes

Reaction equation

HRID 1192544 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([Cl:17])=[CH:9][C:8]=1[C:18](=[O:20])[CH3:19])(=O)=O.[OH:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([N:27]2[CH2:28][CH2:29][CH:24]([OH:23])[CH2:25][CH2:26]2)=[C:8]([C:18](=[O:20])[CH3:19])[CH:9]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 79341Piperidin-4-olHCID 58368456HCID 58368456, compound

Product 1

HCID 58368476HCID 58368476, compoundYield 81%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A stirred mixture of 2-acetyl-4-chloro-1-naphthyl trifluoromethanesulfonate (0.106 g, 0.301 mmol), 4-hydroxypiperidine (0.0366 g, 0.362 mmol), palladium acetate (1 mg, 0.006 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (6 mg, 0.009 mmol), and cesium carbonate (0.14 g, 0.42 mmol) in tetrahydrofuran (6 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate was washed with brine, dried over sodium sulfate and evaporated to dryness. The resulting residue was purified on silica gel, eluting with 0 to 60% ethyl acetate in hexane, to give the desired product (74 mg, 81%). LCMS calculated for C17H19ClNO2 (M+H)+: m/z=304.1; Found: 304.0.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe resulting residue was purified on silica gel
  7. washeluting with 0 to 60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-caa5938f6bb84c489977797f68ba2c23
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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