Triethylamine → 5-Phenylethynyl-pyridin-2-ylamine
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[C:9]1([C:15]#[CH:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCN(CC)CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[C:9]1([C:15]#[C:16][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 65 °C
Procedure
Bis-(triphenylphosphine)-palladium(II)dichloride (320 mg, 0.45 mmol) was dissolved in 50 ml THF and 2-amino-5-iodopyrdine (2.0 g, 9.1 mmol) and phenylacetylene (2.0 ml, 18.2 mmol) were added at room temperature. Et3N (3.8 ml, 27 3 mmol), triphenylphosphine (72 mg, 0.27 mmol) and copper(I)iodide (52 mg, 0.27 mmol) were added and the mixture was stirred for 2 hours at 65° C. The reaction mixture was cooled and extracted once with saturated NaHCO3 solution and three times with ethyl acetate. The organic layers were combined, dried with sodium sulfate, filtered and evaporated to dryness. The crude product was suspended in 5 ml of dichloromethane, stirred for 15 minutes and filtered. The crystals were washed with a small volume of dichloromethane and dried for 1 hour at 50° C. and <20 mbar. The desired compound was obtained as a light yellow solid (1.1 g, 63%), MS: m/e=195.3 (M+H+).
Workup
- temperatureThe reaction mixture was cooled
- extractionextracted once with saturated NaHCO3 solution and three times with ethyl acetate
- dry with materialdried with sodium sulfate
- filtrationfiltered
- customevaporated to dryness
- stirringstirred for 15 minutes
- filtrationfiltered
- washThe crystals were washed with a small volume of dichloromethane
- customdried for 1 hour at 50° C.
Sources & evidence
- ORD record
- ord-4dfb3bfe60af47e58adf20df78faf98f
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716316B2
Reaction notes
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