反応 #2286383

反応方程式

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

K2CO3

6-chloro-3-pyridine boronic acid

ethanol

→

solid

収率 83.0%

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

収率 83.0%

溶媒

ethyl acetate

toluene

反応条件

後処理

1. 1
   温度The mixture was cooled
2. 2
   洗浄The organic layer was washed with saturated aqueous NaHCO3
3. 3
   乾燥dried over Na2SO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他The organic layer was purified by silica gel chromatography (0-100% ethyl acetate/hexanes)

実験手順

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).

出典