N-Methylacetamide → HCID 11717265, compound

HRID 2362859Notes

Reaction equation

HRID 2362859 reaction equation
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.[N:47]12[CH2:54][CH2:53][CH:50]([CH2:51][CH2:52]1)[C@H:49]([NH:55][C:56]([C:58]1[C:62]3[CH:63]=[CH:64][C:65]([Br:67])=[CH:66][C:61]=3S[N:59]=1)=[O:57])[CH2:48]2.C(=O)([O-])[O-:69].[Cs+].[Cs+].CNC(=O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:47]12[CH2:54][CH2:53][CH:50]([CH2:51][CH2:52]1)[C@H:49]([NH:55][C:56]([C:58]1[C:62]3[CH:63]=[CH:64][C:65]([Br:67])=[CH:66][C:61]=3[O:69][N:59]=1)=[O:57])[CH2:48]2

Participants

7

Reactant 4

HCID 6582N-MethylacetamideHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 10044409HCID 10044409, compound

Product 1

HCID 11717265HCID 11717265, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Palladium (II) acetate (0.040 mmol) was added to a solution of (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.050 mmol) in toluene (6 mL) and the reaction mixture was maintained until the contents completely dissolved. The resultant yellow solution was transferred to a mixture of N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1,2-benzisothiazole-3-carboxamide (0.30 mmol), cesium carbonate (0.50 mmol) and N-methylacetamide (0.500 mmol) under an atmosphere of nitrogen gas and the reaction mixture was subjected to microwave irradiation at 200° C. for 300 s. The reaction mixture was filtered through Celite and concentrated. The residue was purified by HPLC, thus providing the product in 50% yield.

Workup

  1. temperaturethe reaction mixture was maintained until the contents
  2. dissolutioncompletely dissolved
  3. customirradiation at 200° C. for 300 s
  4. filtrationThe reaction mixture was filtered through Celite
  5. concentrationconcentrated
  6. customThe residue was purified by HPLC
  7. customthus providing the product in 50% yield

Sources & evidence

ORD record
ord-5a020ddcd80046cdaac551ab686e1b7c
Source dataset
uspto-grants-2014_04
Patent number
US08691841B2

Reaction notes

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