Reaction equation
Br[C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[NH:11]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12]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.CC(C)([O-])C.[Na+]>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].C1(C)C=CC=CC=1>[Cl:8][C:5]1[N:4]=[C:3]([O:9][CH3:10])[C:2]([N:11]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12]2)=[CH:7][CH:6]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A vial was charged 3-bromo-6-chloro-2-methoxypyridine (0.50 g, 2.2 mmol), pyrrolidin-3-ol (0.39 g, 4.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.10 g, 0.10 mmol), Xantphos (0.13 g, 0.20 mmol), sodium tertbutoxide (0.32 g, 3.4 mmol) and toluene (5 mL). The mixture was purged with nitrogen then sealed. The mixture was heated to 100° C. overnight. The mixture was cooled to room temperature, filtered and diluted with 15 mL of water. The solution was extracted with ethyl acetate (10 mL×3). The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel chromatography to give the title compound (29.5 mg, 5.7%) as light brown solid.
Workup
- customThe mixture was purged with nitrogen
- customthen sealed
- temperatureThe mixture was cooled to room temperature
- filtrationfiltered
- additiondiluted with 15 mL of water
- extractionThe solution was extracted with ethyl acetate (10 mL×3)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe resulting residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-d3879e7d894c4300ba61755db370dbbb
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394285B2
Linked notes
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