Cesium carbonate → 4-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

온도

120 °C

To a solution of N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)-2-(2-iodophenoxy)acetamide (100 mg, 0.215 mmol) in dioxane (5 mL) was added Cs2CO3 (139 mg, 0.429 mmol), BINAP (13.3 mg, 0.0215 mmol) and Pd2(dba)3 (8.0 mg, 0.0215 mmol). The reaction mixture was heated at 120° C. for 16 h, cooled to room temperature, filtered, and concentrated. The crude produce was purified by preparative HPLC purification. (23.6 mg, yield 32.5%) MS (ESI+) e/z: 339.2 [M+1]+. 1H NMR (MeOD, 400 MHz), δ ppm: 7.41-7.32 (m, 1H), 7.15-7.06 (m, 3H), 7.06-6.94 (m, 4H), 4.67-4.50 (m, 2H), 4.29-4.13 (m, 2H), 4.07-3.94 (m, 1H), 3.77-3.64 (m, 2H), 2.95-2.83 (m, 3H), 2.83-2.76 (m, 1H), 2.73-2.62 (m, 2H).

1. temperaturecooled to room temperature
2. filtrationfiltered
3. concentrationconcentrated
4. customThe crude produce
5. customwas purified by preparative HPLC purification

ORD 기록

ord-9bd096686a3e4d7695ce07bb57e6437c

출처 데이터셋

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09365555B2