تفاعل #2286383

معادلة التفاعل

(2-bromo-thiazol-5-yl)-methyl-carbamic acid tert-butyl ester

K2CO3

6-chloro-3-pyridine boronic acid

ethanol

→

solid

المردود 83.0%

[2-(6-chloropyridin-3-yl)-thiazol-5-yl]-methyl-carbamic acid tert-butyl ester

المردود 83.0%

المذيبات

ethyl acetate

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was cooled
2. 2
   غسيلThe organic layer was washed with saturated aqueous NaHCO3
3. 3
   تجفيفdried over Na2SO4
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىThe organic layer was purified by silica gel chromatography (0-100% ethyl acetate/hexanes)

الإجراء التجريبي

To a suspension of 6-chloro-3-pyridine boronic acid (158 mg, 1.0 mmol) in toluene (4 mL) was added absolute ethanol (2 mL) followed by a 2.0 M solution of K2CO3 (1.0 mL). To this mixture was added (2-bromo-thiazol-5-yl)-methyl-carbamic acid tert-butyl ester (322 mg, 1.1 mmol) followed by tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol). The reaction mixture was heated to 100° C. for 16 h. The mixture was cooled and diluted with ethyl acetate. The organic layer was washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated. The organic layer was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to afford an off-white solid (270 mg, 83%): mp 167-170° C.; 1H NMR (300 MHz, CDCl3) δ 8.88 (br s, 1H), 8.16 (dd J=3.0, 8.0 Hz, 1H), 7.40 (d, J=7.0 Hz, 1H), 7.39 (s, 1H), 3.45 (s, 3H), 1.61 (s, 9H); ESIMS m/z 326 (M+1).

المصدر