Water → 2-Chloro-8-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[C:22]2[N:23]([N:27]=[C:28]([Cl:30])[N:29]=2)[CH:24]=[CH:25][CH:26]=1.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O.O1CCOCC1>[Cl:30][C:28]1[N:29]=[C:22]2[C:21]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[O:32][CH3:31])=[CH:26][CH:25]=[CH:24][N:23]2[N:27]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 80 °C
Procedure
A Schlenck flask was charged with palladium acetate (0.0966 g, 0.430 mmol), triphenylphosphine (0.4513 g, 1.721 mmol), and 1,4-dioxane (6 mL) and the mixture was stirred for 5 min until it turned bright yellow. 8-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine (0.500 g, 2.15 mmol), 2-methoxybenzeneboronic acid (0.490 g, 3.23 mmol), N,N-dimethylformamide (10.00 mL), and 1.00 N sodium carbonate in water (4.3 mL, 4.3 mmol) were added successively and the reaction was heated at 80° C. overnight, cooled to room temperature, diluted with dichloromethane, filtered through diatomaceous earth and concentrated. The reaction was purified via chromatography (silica gel 10%→20% ethyl acetate in hexanes) and concentrated to give 2-chloro-8-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (0.464 g, 83%). MS=260 (MH)+.
Workup
- temperaturecooled to room temperature
- filtrationfiltered through diatomaceous earth
- concentrationconcentrated
- customThe reaction was purified via chromatography (silica gel 10%→20% ethyl acetate in hexanes)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f109df04bdb84d7c8c67e18bc58d97c9
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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