Cesium carbonate → HCID 86603157, compound
Reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[C:62](=[NH:75])([C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:62](=[N:75][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])([C:69]1[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=1)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1Participants
7
Conditions
- Temperature
- 100 °C
Procedure
2-Chloro-6,N-dimethoxy-N-methyl-isonicotinamide (1.0 g, 4.35 mmol) was added to a mixture of Pd(OAc)2 (0.05 g, 0.22 mmol), BINAP (0.27 g, 0.43 mmol), benzophenone imine (0.88 mL, 5.22 mmol), and cesium carbonate (7.08 g, 21.7 mmol) in toluene (16 mL) and heated to 100° C. for 12 h. Pd(OAc)2 (0.05 g, 0.22 mmol) was added to the reaction mixture and stirred for an additional 1 h at 100° C. The reaction mixture was cooled to room temperature, quenched with EtOAc (200 mL), and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (ethyl acetate/hexanes 65:35) to afford the title compound as a yellow oil (1.53 g, 94%). MS: 376.3 (MH+); HPLC Rf: 6.92 min. (HPLC method 4).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customquenched with EtOAc (200 mL)
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
- customthe residue was purified by flash column chromatography (ethyl acetate/hexanes 65:35)
Sources & evidence
- ORD record
- ord-e8bc7ae9fe56476b80fdf6995f67f31b
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595325B2
Reaction notes
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