تفاعل #85779

معادلة التفاعل

N2

(S)-tert-butyl(1-(5-bromo-4-methylpyridin-2-yl)ethyl)carbamate

(2-(trifluoromethyl)pyridin-4-yl)boronic acid

Na2CO3

→

(S)-tert-butyl(1-(4-methyl-2′-(trifluoromethyl)-[3,4′-bipyridin]-6-yl)ethyl)carbamate

المردود 82.6%

المذيبات

dioxane

EtOAc

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with water, brine
2. 2
   تجفيفdried over Na2SO4
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   أخرىpurified through flash column chromatography (0-100% EtOAc/Heptane)

الإجراء التجريبي

N2 was bubbled through a solution of (S)-tert-butyl(1-(5-bromo-4-methylpyridin-2-yl)ethyl)carbamate (200 mg, 0.635 mmol), (2-(trifluoromethyl)pyridin-4-yl)boronic acid (145 mg, 0.761 mmol) and Na2CO3 (2.0 M, 635 μl, 1.269 mmol) in dioxane for 5 min. Cl2Pd(dppf) (CH2Cl2 adduct) (51.8 mg, 0.063 mmol) was added. The reaction mixture was stirred at 90° C. for 16 hr. The mixture was diluted with EtOAc, washed with water, brine, dried over Na2SO4, filtered, concentrated and purified through flash column chromatography (0-100% EtOAc/Heptane) to give 200 mg (S)-tert-butyl(1-(4-methyl-2′-(trifluoromethyl)-[3,4′-bipyridin]-6-yl)ethyl)carbamate as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.83 (d, J=4.9 Hz, 1H), 8.36 (s, 1H), 7.66 (s, 1H), 7.51-7.42 (m, 1H), 7.21 (s, 1H), 5.60 (d, J=7.7 Hz, 1H), 4.87 (p, J=6.9 Hz, 1H), 2.30 (s, 3H), 1.48 (d, J=6.9 Hz, 3H), 1.45 (s, 9H). MS m/z 382.3 (M+H).

المصدر