Cesium carbonate → HCID 67247975, compound

HRID 1192651Notes

Reaction equation

HRID 1192651 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:33])[CH3:32])[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>[C:18]([C:8]1[C:7]([N:24]2[CH2:29][CH2:28][CH:27]([NH:30][C:31](=[O:33])[CH3:32])[CH2:26][CH2:25]2)=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[N:15]2)=[C:10]([Cl:17])[CH:9]=1)(=[O:20])[CH3:19]

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 114011054-Acetamidopiperidine dihydrochlorideHCID 58368658HCID 58368658, compound

Product 1

HCID 67247975HCID 67247975, compoundYield 55.2%

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 (0.17 g, 0.25 mmol, from Example 47, Step 2), N-piperidin-4-ylacetamide hydrochloride (0.040 g, 0.22 mmol), palladium acetate (1.0 mg, 0.0045 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (4.2 mg, 0.0067 mmol), and cesium carbonate (0.28 g, 0.85 mmol) in tetrahydrofuran (4 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 purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product (42 mg, 54%). LCMS calculated for C18H21ClN3O2 (M+H)+: m/z=346.1; Found: 346.1.

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% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-f5bdd9ef08cf48acb2bdaa8cb2d5059e
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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