Tetrahydrofuran → HCID 58368537, compound

HRID 1192645Notes

Reaction equation

HRID 1192645 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[CH2:28][CH2:27][C@H:26]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[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[CH2:28][CH2:27][C@H:26]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[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 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 58368658HCID 58368658, compoundHCID 672492061312686-83-1

Product 1

HCID 58368537HCID 58368537, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 6344DichloromethaneSolvent

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-[(3S)-pyrrolidin-3-yl]methanesulfonamide hydrochloride (0.062 g, 0.31 mmol), palladium acetate (1.1 mg, 0.0049 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (4.6 mg, 0.0074 mmol), and cesium carbonate (0.31 g, 0.94 mmol) in tetrahydrofuran (4 mL, 50 mmol) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate were washed with brine, dried over MgSO4, evaporated and purified on silica gel (eluting with 0 to 5% methanol in dichloromethane) to give the desired product (37 mg, 41%). LCMS calculated for C16H19ClN3O3S (M+H)+: m/z=368.1; Found: 368.1.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe filtrate were 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-784dca1b93a54342b18f8375997f33cb
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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