Sodium Carbonate → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-2,2-dimethyl-propionamide
Reaction equation
[CH3:1][CH:2]([CH3:13])[C:3]([NH:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1I)=[O:4].[C:14](=O)([O-])[O-].[Na+].[Na+].[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:11]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[NH:5][C:3](=[O:4])[C:2]([CH3:13])([CH3:14])[CH3:1]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 35 g (115 mmol) 2,2-dimethyl-N-(4-iodo-pyridin-3-yl)-acetamide, 400 ml toluene, 120 ml 2 N sodium carbonate solution, 4.0 g (3.5 mmol) tetrakis(triphenylphosphine)palladium(0) and 20.0 g (128 mmol) o-chlorophenylboronic acid was heated under argon at 80° C. for 12 h. After cooling to room temperature, the aqueous phase was separated and washed twice with toluene. The combined organic layers were washed with 50 ml brine, dried (magnesium sulfate) and evaporated. The residue was purified by flash chromatography to yield 21.6 g (65%) of the title compound as white crystals.
Workup
- temperatureAfter cooling to room temperature
- customthe aqueous phase was separated
- washwashed twice with toluene
- washThe combined organic layers were washed with 50 ml brine
- dry with materialdried (magnesium sulfate)
- customevaporated
- customThe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-52db1704da534c5881145ba44c5ba15a
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06297375B1
Reaction notes
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