1,2-Dimethoxyethane → 1,3-Dimethoxy-2-(Tol-2-yl)-4-(Pyrid-3-yl)-Benzene
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](Br)=[C:14]([O:19][CH3:20])[C:13]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27].C(COC)OC.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][C:17]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[C:12]([O:11][CH3:10])[C:13]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Pyridine-3-boronic acid (5.81 g, 47.27 mmol, Frontier Scientific, Inc.), 1,3-dimethoxy-2-(tol-2-yl)-4-bromobenzene (2) (10.7 g, 34.8mmol), glyme (200 mL), and tetrakis(triphenylphosphine) palladium (Ph3P)4Pdo (4 g, 3.46 mmol) were stirred for 15 minutes followed by the addition of potassium carbonate (16 g in 70 ml of water). After refluxing for 10 hr, the reaction mixture was poured into 800 ml of 1:1 mixture of water and ethyl acetate. The organic layer was washed with water (300 ml×2) and brine (200 ml), the solvent was removed, and the crude product was purified by silica-gel chromatography eluting with hexane and ethyl acetate (10% to 25% ethyl acetate) yielding 8.8 g (83%) of 3.
Workup
- temperatureAfter refluxing for 10 hr
- washThe organic layer was washed with water (300 ml×2) and brine (200 ml)
- customthe solvent was removed
- customthe crude product was purified by silica-gel chromatography
- washeluting with hexane and ethyl acetate (10% to 25% ethyl acetate)
Sources & evidence
- ORD record
- ord-5f953a7b394a4eb08ee60c672c3744d9
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06221604B1
Reaction notes
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