Sodium Carbonate → (Z)-N-(1-(4-bromophenyl)-1-(3-thienyl)prop-1-en-3-yl)sarcosine

온도

90 °C

To a solution of (Z)-N-(1-(4-bromophenyl)-1-iodoprop-1-en-3-yl)sarcosine, tbutyl ester D (29.86 g, 64.06 mmol) in dimethoxyethane (300 mL) was added 3-thiopheneboronic acid (9.02 g, 70.47 mmol), Pd(PPh3)4 (3.70 g, 3.20 mmol), and 2M Na2CO3 (300 mL). The reaction was warmed to 90° C. with vigorous mechanical stirring for 4.5 hours. The mixture was cooled, and partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4), filtered, and concentrated. Column chromatography (2-5% acetone/hexanes) provided (Z)-N-(1-(4-bromophenyl)-1-(3-thienyl)prop-1-en-3-yl)sarcosine, tbutyl ester E(i) (27.06 g, 78%) as a yellow oil. 1H NMR (300 MHz, CDCl3) 1.43 (s, 9H), 2.36 (s, 3H), 3.14 (s, 2H), 3.28 (d, 2H), 6.16 (7, 1H), 6.86 (d, 1H), 7.12-7.14 (m, 3H), 7.32 (collapsed dd, 1H), 7.41 (d, 2H).

1. temperatureThe mixture was cooled
2. custompartitioned between EtOAc and water
3. washThe organic phase was washed with brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated

ORD 기록

ord-96971c04564c428b9ac37acd34e9065e

출처 데이터셋

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06667336B2