Cesium carbonate → HCID 58368496, compound

HRID 1192629Notes

Reaction equation

HRID 1192629 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([Cl:17])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)(=O)=O.[N:23]1[CH:28]=[CH:27][C:26]([CH2:29][N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:25][CH:24]=1.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.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:17][C:10]1[CH:9]=[C:8]([C:18](=[O:20])[CH3:19])[C:7]([N:33]2[CH2:34][CH2:35][N:30]([CH2:29][C:26]3[CH:25]=[CH:24][N:23]=[CH:28][CH:27]=3)[CH2:31][CH2:32]2)=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 8087151-((Pyridin-4-yl)methyl)piperazineHCID 58368658HCID 58368658, compound

Product 1

HCID 58368496HCID 58368496, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (0.12 g, 0.34 mmol, from Example 47, Step 2), 1-(pyridin-4-ylmethyl)piperazine (0.072 g, 0.41 mmol), palladium acetate (1.5 mg, 0.0067 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (6.3 mg, 0.010 mmol), and cesium carbonate (0.31 g, 0.95 mmol) in tetrahydrofuran (3 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate was washed with brine, dried over MgSO4 and evaporated. The resulting residue was purified on silica gel (eluting with 0 to 10% methanol in dichloromethane) to give the desired product (20.2 mg, 16%). LCMS calculated for C21H22ClN4O (M+H)+: m/z=381.1; Found: 381.1.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe resulting residue was purified on silica gel (eluting with 0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ae319ebb484940e1bbeaa1195e76021d
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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