Potassium Phosphate, Tribasic → 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([NH:15][CH3:16])=[O:14].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:7]=[C:6]([NH:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([NH:15][CH3:16])=[O:14])[C:5]([Cl:9])=[CH:4][N:3]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
A 150-mL sealed tube was charged with 2,5-dichloro-4-iodopyridine (3.5 g, 12.78 mmol), 2-amino-N-methylbenzamide (1.919 g, 12.78 mmol) and tripotassium phosphate (8.14 g, 38.3 mmol) in 1,4-dioxane (100 mL). The reaction mixture was degassed with nitrogen for 10 min. Bis(2-diphenylphosphinophenyl)ether (DPEPhos, 0.688 g, 1.278 mmol) and Pd(OAc)2 (0.115 g, 0.511 mmol) were added and the reaction mixture was heated in a 120° C. oil bath over night. The reaction mixture was filtered through celite, which was washed with dioxane. The solvent was evaporated to dryness and the solid was washed with EtOH (10 mL×3) to give 2.14 g (56%) of product as an off white solid.
Workup
- customA 150-mL sealed tube
- customThe reaction mixture was degassed with nitrogen for 10 min
- filtrationThe reaction mixture was filtered through celite, which
- washwas washed with dioxane
- customThe solvent was evaporated to dryness
- washthe solid was washed with EtOH (10 mL×3)
Sources & evidence
- ORD record
- ord-1fb034e559f741f5b654f8ae1d4bc749
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012479B2
Reaction notes
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