Sodium Carbonate → 1-(4-benzylphenyl)-9-(4-hydroxyphenyl)benzo[h][1,6]naphthyridin-2(1H)one

온도

100 °C

To a solution of 1-(4-benzylphenyl)-9-chlorobenzo[h][1,6]naphthyridin-2(1H)-one (100 mg, 0.22 mmol) in 1,4-dioxane (0.6 mL) was added 4-hydroxyphenylboronic acid (45 mg, 0.33 mmol) and 1 N Na2CO3 (0.66 mL, 0.66 mmol). The reaction mixture was degassed using Argon gas for 10 min and added Pd(PPh3)2Cl2 (15 mg, 0.02 mmol) and di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (15 mg, 0.04 mmol). The reaction flask was put into the preheated oil-bath at 100° C. The reaction mixture was further stirred at 100° C. a period of 8 hours after which, it was filtered and partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Mg504, filtered and concentrated. The crude product was purified by flash column chromatography using a 97:3 v/v CH2Cl2:EtOH as solvent to afford title compound (64 mg, 64% yield) as a yellow solid. 1H NMR 600 MHz (CDCl3) δ 9.08 (s, 1H), 8.42 (s, 1H), 8.04 (d, J=2.4 Hz, 1H), 7.95 (d, J=8.2 Hz, 1H), 7.61 (dd, J=2.1, 6.6 Hz, 1H), 7.25 (m, 2H), 7.12 (m, 4H), 7.00 (m, 5H), 6.75 (d, J=8.4 Hz, 2H), 6.48 (dd, J=2.4, 6.2 Hz, 1H), 3.88 (s, 2H), MS m/z: 455.27 (M+1).

1. customThe reaction mixture was degassed
2. customfor 10 min
3. customwas put into the preheated oil-bath at 100° C
4. filtrationwas filtered
5. custompartitioned between ethyl acetate and water
6. customThe organic layer was separated
7. extractionthe aqueous layer was extracted with ethyl acetate
8. washThe combined organic extracts were washed with brine
9. customdried over Mg504
10. filtrationfiltered
11. concentrationconcentrated
12. customThe crude product was purified by flash column chromatography

ORD 기록

ord-bd09652d47ef44b8936d5ca95e6ca3b1

출처 데이터셋

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08889706B2