Cesium carbonate → HCID 178479985, compound
Reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][N:4](C(OC(C)(C)C)=O)[N:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Br[C:57]1[C:58](=[O:65])[N:59]([CH3:64])[CH:60]=[C:61]([Br:63])[CH:62]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[NH:4]1[CH:5]=[CH:6][C:2]([NH:1][C:57]2[C:58](=[O:65])[N:59]([CH3:64])[CH:60]=[C:61]([Br:63])[CH:62]=2)=[N:3]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 105 °C
Procedure
A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 289a (2.2 g, 12 mmol), XantPhos (0.69 g, 1.2 mmol), Pd2(dba)3 (1.1 g, 1.2 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (6.4 g, 24 mmol), Cs2CO3 (15.6 g, 48 mmol), and 1,4-dioxane (50 mL). After bubbling nitrogen through the resulting mixture for 10 minutes, it was heated at 105° C. for 15 h. The mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue the mixture was washed with methanol (8 mL) to afford 289b as a pale yellow solid (1.2 g, 37%). MS-ESI: [M+H]+ 269.1.
Workup
- customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
- customAfter bubbling nitrogen through the resulting mixture for 10 minutes
- temperatureThe mixture was cooled to room temperature
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
- washthe residue the mixture was washed with methanol (8 mL)
Sources & evidence
- ORD record
- ord-44f0a2917b1640da8a634f078b9cbe43
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921353B2
Reaction notes
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