Potassium Carbonate → HCID 59856620, compound

HRID 2360484Notes

Reaction equation

HRID 2360484 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C12BC(CCC1)CCC2.FC(F)(F)S(O[C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:38]=1[N:37]([CH3:39])[C:36]([C:40](=[O:59])[NH:41][C:42]1[CH:47]=[C:46]([C:48]([CH3:51])([CH3:50])[CH3:49])[CH:45]=[C:44]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])[C:43]=1[O:57][CH3:58])=[CH:35]2)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CN(C)C=O.O.C(OCC)(=O)C.ClCCl>[C:48]([C:46]1[CH:45]=[C:44]([NH:52][S:53]([CH3:56])(=[O:54])=[O:55])[C:43]([O:57][CH3:58])=[C:42]([NH:41][C:40]([C:36]2[N:37]([CH3:39])[C:38]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][C:30]=3[CH2:1][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)=[O:59])[CH:47]=1)([CH3:51])([CH3:49])[CH3:50]

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 27568081-Boc-4-MethylenepiperidineHCID 58608280HCID 58608280, compound

Product 1

HCID 59856620HCID 59856620, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 620 mg tert-butyl 4-methylene-piperidine-1-carboxylate and 6.3 ml of a 0.5 M solution of 9-borabicyclo[3.3.1]nonane in tetrahydrofuran is heated for one hour to 80° C. under argon. The solution thus prepared is added under argon to a mixture of 1.8 g 2-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenylcarbamoyl)-1-methyl-1H-indol-7-yl trifluoro-methanesulphonate, 3.5 g potassium carbonate and 253 mg [1,1′-bis(diphenylphosphino)-ferrocen]dichloropalladium(II) complex with dichloromethane (1:1) in 12 ml N,N-dimethylformamide and 1.2 ml of water. The mixture is heated for 3 hours to 60° C., the solvents are eliminated in vacuo, taken up in ethyl acetate and the insoluble ingredients are filtered off. The filtrate is washed twice with water and once with saturated aqueous sodium chloride solution. After drying with magnesium sulphate the solvent is eliminated in vacuo and the residue is chromatographed on silica gel with cyclohexane/ethyl acetate 80:20 to 20:80.

Workup

  1. temperatureis heated for one hour to 80° C. under argon
  2. customThe solution thus prepared
  3. temperatureThe mixture is heated for 3 hours to 60° C.
  4. filtrationthe insoluble ingredients are filtered off
  5. washThe filtrate is washed twice with water and once with saturated aqueous sodium chloride solution
  6. dry with materialAfter drying with magnesium sulphate the solvent
  7. customthe residue is chromatographed on silica gel with cyclohexane/ethyl acetate 80:20 to 20:80

Sources & evidence

ORD record
ord-5273bf9e209e4826aa846ba74dce1573
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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