Trimethylsilylacetylene → 5-(Trifluoromethyl)-3-((trimethylsilyl)ethynyl)-pyridin-2-amine
Reaction equation
I[C:2]1[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Si:13]([C:17]#[CH:18])([CH3:16])([CH3:15])[CH3:14]>C1COCC1.C(OCC)(=O)C.[Cu](I)I>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:7]=[C:2]([C:18]#[C:17][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:3]([NH2:12])=[N:4][CH:5]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To a stirred solution of 3-Iodo-5-trifluoromethylpyridin-2-amine (61.38 g, 213 mmol) in anhydrous THF (200 mL) under a nitrogen atmosphere was added Pd(PPh)3Cl2 (1.5 g, 2.1 mmol), and copper iodide (0.406 g, 2.1 mmol) and the reaction mixture degassed under nitrogen. The reaction mixture was cooled in an ice bath and TMS acetylene (36 mL, 256 mmol) was added dropwise over 30 minutes. Upon complete addition the reaction was allowed to warm to room temperature and monitored until the reaction was complete. The mixture was diluted with ethyl acetate (200 mL) and filtered through silica washed through with 4×150 mL ethyl acetate. The filtrates were concentrated and the solid was triturated from heptane (250 mL) to give 56 g of product.
Workup
- customthe reaction mixture degassed under nitrogen
- temperatureThe reaction mixture was cooled in an ice bath
- additionUpon complete addition the reaction
- filtrationfiltered through silica
- washwashed through with 4×150 mL ethyl acetate
- concentrationThe filtrates were concentrated
- customthe solid was triturated from heptane (250 mL)
Sources & evidence
- ORD record
- ord-415e3afb35404a76a262688e1c89e3a3
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08530489B2
Reaction notes
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