Reaction equation
C1(C2C3C(=CC=CC=3)C=CC=2)C2C(=CC=CC=2)C=CC=1P(C(C)(C)C)C(C)(C)C.Br[C:31]1[N:36]=[C:35]([O:37][CH3:38])[C:34]([N+:39]([O-:41])=[O:40])=[CH:33][CH:32]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:48]([O:52][C:53]([N:55]1[CH2:59][CH2:58][CH2:57][C@H:56]1[CH2:60][OH:61])=[O:54])([CH3:51])([CH3:50])[CH3:49]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:48]([O:52][C:53]([N:55]1[CH2:59][CH2:58][CH2:57][C@H:56]1[CH2:60][O:61][C:31]1[CH:32]=[CH:33][C:34]([N+:39]([O-:41])=[O:40])=[C:35]([O:37][CH3:38])[N:36]=1)=[O:54])([CH3:51])([CH3:50])[CH3:49]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of Pd(OAc)2 (0.08 g, 0.34 mmol) and [1,1′]binaphthalen-2-yl-di-tert-butyl-phosphane (0.14 g, 0.34 mmol) in toluene (10 ml) was added 6-bromo-2-methoxy-3-nitropyridine(1.0 g, 4.29 mmol), Cs2CO3 (3.5 g, 10.73 mmol), and (S)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.73 g, 8.58 mmol). The mixture was stirred under nitrogen at room temperature for 24 h. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel chromatography with dichloromethane/ethyl acetate/methanol (10:0:0; 9:0.5:0.5; 7:1.5:1.5; 0:5:5) as eluent to provide 0.11 g (7.5%) of the product.
Workup
- customAfter evaporation of the solvent under reduced pressure
- customthe residue was purified by silica gel chromatography with dichloromethane/ethyl acetate/methanol (10:0:0; 9:0.5:0.5; 7:1.5:1.5; 0:5:5) as eluent
Sources & evidence
- ORD record
- ord-daa5133780a24e8ea1a1896e1fb710be
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383641B2
Linked notes
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