Cesium carbonate → HCID 68280491, compound

HRID 1192654Notes

Reaction equation

HRID 1192654 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.Cl.[NH:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:31](=[O:34])[O:32][CH3:33])[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>[CH3:33][O:32][C:31](=[O:34])[NH:30][CH:27]1[CH2:26][CH2:25][N:24]([C:7]2[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([Cl:17])=[C:11]3[C:16]=2[N:15]=[CH:14][CH:13]=[CH:12]3)[CH2:29][CH2:28]1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 58368658HCID 58368658, compoundHCID 67248274955027-84-6

Product 1

HCID 68280491HCID 68280491, compoundYield 41.5%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
65 °C

Procedure

A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (0.12 g, 0.17 mmol, from Example 47, Step 2), methyl piperidin-4-ylcarbamate hydrochloride (0.028 g, 0.14 mmol), palladium acetate (0.64 mg, 0.0029 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (2.7 mg, 0.0043 mmol), and cesium carbonate (0.18 g, 0.55 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, evaporated and then purified on silica gel (eluting with 0 to 5% methanol in dichloromethane) to give the desired product (21 mg, 40%). LCMS calculated for C18H21ClN3O3 (M+H)+: m/z=362.1; Found: 362.1.

Workup

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

Sources & evidence

ORD record
ord-254871578aeb42cd84135d273f78531c
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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