Sodium Carbonate → HCID 5329381, 화합물

온도

90 °C

1-(tert-Butoxycarbonyl)-5-{[4-(tert-butoxycarbonyl)piperazin-1-yl]sulfonyl}-1H-indol-2-ylboronic acid (2-3, 1.88 g, 3.69 mmol, 2.0 equiv) was added in four equal portions at 30 minute intervals to a solution of 3-iodo-1H-quinolin-2-one (1-3, 0.500 g, 1.84 mmol, 1 equiv), lithium chloride (0.235 g, 5.54 mmol, 3.00 equiv), tetrakis(triphenylphosphine)palladium (0.107 g, 0.093 mmol, 0.050 equiv), and aqueous sodium carbonate solution (2 M, 4.61 mL, 9.22 mmol, 5.00 equiv) in dioxane (50 mL) at 90° C. The reaction mixture was heated for 2 h at 90° C. following the final addition. The mixture was then partitioned between brine (100 mL) and EtOAc (2×100 mL). The combined organic layers were dried over sodium sulfate and concentrated. A solution of the residue in dichloromethane (100 mL) was treated with trifluoroacetic acid (100 mL), and the resulting mixture was stirred for 45 minutes, then concentrated. The residue was purified by reverse-phase liquid chromotography (H2O/CH3CN gradient w/0.1% TFA present) to give 3-[5-(piperazin-1-ylsulfonyl)-1H-indol-2-yl]quinolin-2(1H)-one (2-4) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 12.23 (br s, 1H), 12.11 (s, 1H), 8.62 (s, 1H), 8.00 (br s, 1H), 7.77 (d, 1H, J=7.8 Hz), 7.74 (d, 1H, J=8.6 Hz), 7.56 (t, 1H, J=7.8 Hz), 7.51 (s, 1H), 7.44 (d, 1H, J=8.6 Hz), 7.40 (d, 1H, J=8.1 Hz), 7.27 (t, 1H, J=7.8 Hz), 2.77 (m, 4H), 2.71 (m, 4H).

1. additionaddition
2. customThe mixture was then partitioned between brine (100 mL) and EtOAc (2×100 mL)
3. dry with materialThe combined organic layers were dried over sodium sulfate
4. concentrationconcentrated
5. additionA solution of the residue in dichloromethane (100 mL) was treated with trifluoroacetic acid (100 mL)
6. concentrationconcentrated
7. customThe residue was purified by reverse-phase liquid chromotography (H2O/CH3CN gradient w/0.1% TFA present)

ORD 기록

ord-e19ccf435d3241d685e475346cc35fea

출처 데이터셋

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07169788B2