6-(1H-pyrazol-1-yl)-2,2'-bipyridine synthesis
- Product Name:6-(1H-pyrazol-1-yl)-2,2'-bipyridine
- CAS Number:135853-33-7
- Molecular formula:C13H10N4
- Molecular Weight:222.25
Yield: 87%
Reaction Conditions:
Stage #1:NH-pyrazole with sodium t-butanolate in dimethyl sulfoxide at 20; for 0.166667 h;Inert atmosphere;
Stage #2:6-fluoro-2,2′-bipyridine in dimethyl sulfoxide at 100; for 24 h;
Steps:
1 6-(1H-pyrazol-1-yl)-2,2'-bipyridine:
To an oven dried, N2 filled round bottom flask was added lH-pyrazole (479 mg, 7.04 mmol), sodium tert-butoxide (678 mg, 7.06 mmol), and 5 ml of N2-degassed, dry DMSO at room temperature. Note: reaction gives off heat. After stirring for 10 minutes the reaction ceased to give off heated. 6-fluoro-2,2'-bipyridine (1.2 g, 6.89 mmol) was added in one portion. The reaction was heated to 100°C with stirring and monitored by TLC. After 24 hours, the reaction was cooled to room temperature and the mixture was extracted with Et20 (-100 mL) and H2O (-100 mL). The organics were separated and dried with Na2S04. The concentrated mixture was then purified by silica gel chromatography first by eluting 100% DCM to remove any excess pyrazole, then 50% MeOH/DCM to give a white solid (1.3 g, 5.99 mmol, 87% yield). NMR (300 MHz, de-DMSO) δ 8.92 (d, 7= 1.8 Hz, 1H), 8.72 (d, 7= 3.8 Hz, 1H), 8.58 (dd, 7= 7.7, 0.8 Hz, 1H) 8.33 (d, 7= 7.7 Hz, 1H), 8.11 (t, 7= 7.7 Hz, 1H), 8.05-7.95 (m, 2H), 7.87 (d, 7= 0.7 Hz, 1H), 7.51 (dd, 7= 7.7 ,4.8 Hz, 1H), 6.64 (ap t, 7= 1.6 Hz, 1H). This molecule was previously prepared through an alternate procedure and the characterization data was in agreement.
References:
UNIVERSITY OF MISSISSIPPI;DELCAMP, Jared Heath;RODRIGUES, Roberta Ramalho;PEDDAPURAM, Adithya;CHEEMA, Hammad Arshad WO2019/23436, 2019, A1 Location in patent:Paragraph 00105; 00108-00109
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