3-(4-METHYLPHENYL)PYRIDINE synthesis
- Product Name:3-(4-METHYLPHENYL)PYRIDINE
- CAS Number:4423-09-0
- Molecular formula:C12H11N
- Molecular Weight:169.22
1120-90-7
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Yield:4423-09-0 99%
Reaction Conditions:
with potassium phosphate;palladium diacetate;triphenylphosphine in N,N-dimethyl-formamide at 90; for 1 h;Schlenk technique;Inert atmosphere;
Steps:
4.2.1 Reaction of 3-iodopyridine with BiPh3 reagent (for Table 1)
General procedure: An oven dried Schlenk tube was purged with nitrogen and charged with 3-iodopyridine (0.875 mmol, 179.3 mg), BiPh3 (0.25 mmol, 110 mg), K3PO4 (1.5 mmol, 318 mg), Pd(OAc)2 (0.025 mmol, 5.6 mg), PPh3 (0.1 mmol, 26.2 mg) followed by dry DMF (3 mL) under nitrogen atmosphere. The reaction mixture was stirred in an oil bath at 90°C for 1h. It was brought to rt, treated with water (10mL), and extracted with ethyl acetate (2×20 mL). The organic extract was treated with brine, dried over anhydrous MgSO4, and concentrated using rotary evaporator under the reduced pressure. The crude was subjected to silica gel column chromatography (5% EtOAc/Hexane) to obtain 3-phenylpyridine (1.1) as colorless oil (115 mg, 98%).
References:
Rao, Maddali L.N.;Dhanorkar, Ritesh J. [Tetrahedron,2015,vol. 71,# 2,p. 338 - 349]
