Cesium carbonate → HCID 58368639, compound

HRID 1192639Notes

Reaction equation

HRID 1192639 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.[CH3:24][CH:25]([CH3:34])[C:26]([NH:28][C@H:29]1[CH2:33][CH2:32][NH:31][CH2:30]1)=[O:27].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:31]2[CH2:32][CH2:33][C@H:29]([NH:28][C:26](=[O:27])[CH:25]([CH3:24])[CH3:34])[CH2:30]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 58368658HCID 58368658, compoundHCID 67302068HCID 67302068, compound

Product 1

HCID 58368639HCID 58368639, compoundYield 47.9%

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, 0.24 mmol, from Example 47, Step 2), 2-methyl-N-[(3S)-pyrrolidin-3-yl]propanamide hydrochloride (0.035 g, 0.18 mmol), palladium acetate (0.82 mg, 0.0036 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (3.4 mg, 0.0054 mmol), and cesium carbonate (0.22 g, 0.69 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 and evaporated under reduced pressure. The residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product (31 mg, 47%). LCMS calculated for C19H23ClN3O2 (M+H)+: m/z=360.1; Found: 360.1.

Workup

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

Sources & evidence

ORD record
ord-6e7bf053eb7840dc9842bbb544355075
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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