تفاعل #689279

معادلة التفاعل

2-fluoro phenylboronic acid

tert-butyl 6-bromonicotinate

→

desired product

المردود 42.2%

tert-butyl 6-(2-fluorophenyl)nicotinate

المردود 42.2%

ظروف التفاعل

المعالجة

1. 1
   أخرىthe mixture was evacuated 3× with N2
2. 2
   workup.DISSOLUTIONThe solids were dissolved in 25 mL of DMF
3. 3
   workup.ADDITIONfollowed by addition of 2.9 mL of 2 M cesium carbonate
4. 4
   درجة الحرارةThe mixture was cooled to room temperature
5. 5
   workup.ADDITIONpoured into a seperatory funnel
6. 6
   workup.ADDITIONfollowed by addition of EtOAc and water (1×200 mL)
7. 7
   أخرىThe layers were separated
8. 8
   استخلاصthe organic extract
9. 9
   غسيلwashed with brine (1×200 mL), dried MgSO4
10. 10
    ترشيحfiltered
11. 11
    تركيزconcentrated
12. 12
    أخرىto afford an orange oil
13. 13
    أخرىThe crude mixture was purified by chromatography (silica, 10% EtOAc:Heptane)

الإجراء التجريبي

To a round-bottom flask was added 2-fluoro phenylboronic acid (271 mg, 1.94 mmol), palladium tetrakis(triphenylphosphine) (22.4 mg, 0.0194 mmol)) and tert-butyl 6-bromonicotinate (500 mg, 1.94 mmol) and the mixture was evacuated 3× with N2. The solids were dissolved in 25 mL of DMF, followed by addition of 2.9 mL of 2 M cesium carbonate. The resulting mixture was heated to ˜90° C. The mixture was cooled to room temperature and then poured into a seperatory funnel, followed by addition of EtOAc and water (1×200 mL). The layers were separated and the organic extract washed with brine (1×200 mL), dried MgSO4, filtered and concentrated to afford an orange oil. The crude mixture was purified by chromatography (silica, 10% EtOAc:Heptane) to afford the desired product (224 mg, 40%). 1H NMR (400 MHz, DMSO-d6) □ ppm 9.16 (1H, d, J=2.2 Hz), 8.34 (1H, dd, J=8.3, 2.3 Hz), 7.90-8.05 (2H, m), 7.50-7.62 (1H, m), 7.33-7.44 (2H, m) 1.59 (9 H, s).

المصدر