N-Methylacetamide → HCID 11717265, compound
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]2Participants
7
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
- temperaturethe reaction mixture was maintained until the contents
- dissolutioncompletely dissolved
- customirradiation at 200° C. for 300 s
- filtrationThe reaction mixture was filtered through Celite
- concentrationconcentrated
- customThe residue was purified by HPLC
- customthus providing the product in 50% yield
Sources & evidence
- ORD record
- ord-59579f01850c414688ecc5fa35a4c56b
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263619B2
Reaction notes
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