Cesium carbonate → HCID 58368603, compound

HRID 1192642Notes

Reaction equation

HRID 1192642 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][C:30](=[O:33])[O:31][CH3:32])[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>[CH3:32][O:31][C:30](=[O:33])[NH:29][C@H:26]1[CH2:27][CH2:28][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)[CH2:25]1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 58368658HCID 58368658, compoundHCID 118918483HCID 118918483, compound

Product 1

HCID 58368603HCID 58368603, compoundYield 71.1%

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 (0.16 g, 0.23 mmol, from Example 47, Step 2), methyl (3S)-pyrrolidin-3-ylcarbamate hydrochloride (0.035 g, 0.19 mmol), palladium acetate (0.87 mg, 0.0039 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (3.6 mg, 0.0058 mmol), and cesium carbonate (0.24 g, 0.74 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. The residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product (47 mg, 70%). LCMS calculated for C17H19ClN3O3 (M+H)+: m/z=348.1; Found: 348.4.

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 residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-3841005af9cd4e848a2648c0ced9ff06
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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