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The Journal of Organic Chemistry
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6.7 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) δ 162.1, 153, 151.5, 148.1, 145.1, 140.4, 137.3, 130, 129.8, 124.4, 123.6, 123.5,
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121.5, 119.4, 116.7, 107.5. FT-IR: = 3412, 3069, 2959, 2859, 2762, 2704, 2569, 2365, 1654, 1603, 1576, 1543, 1497, 1467,
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1435, 1420, 1277, 1209 cm-1. HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C16H1235ClN2O2 299.0582; Found 299.0588.
6-(5-Bromo-2-hydroxyphenyl)-1-(pyridin-2-yl)pyridine-2(1H)-one (4g): Yield 65% (22.2 mg), brown amorphous solid,
1H NMR (600 MHz, DMSO-d6) δ 10.09 (s, 1H), 8.29 (d, J = 4.7 Hz, 1H), 7.80 (t, J = 7.6 Hz, 1H), 7.57 (dd, J = 9.3, 6.8 Hz,
1H), 7.42 (d, J = 7.9 Hz, 1H), 7.27 (dd, J = 7.4, 4.9 Hz, 1H), 7.24 – 7.11 (m, 2H), 6.54 (dd, J = 21.3, 8.9 Hz, 2H), 6.25 (d, J =
6.7 Hz, 1H). 13C NMR (150 MHz, DMSO-d6) δ 162.2, 153.6, 151.5, 148.2, 145.0, 140.6, 137.4, 132.9, 132.7, 124.5, 124.2,
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123.6, 119.4, 117.3, 109, 107.7. FT-IR: = 3436, 3044, 3021, 2959, 2925, 2854, 2673, 2545, 1672, 1602, 1560, 1546, 1491,
1468, 1438, 1420, 1370, 1290 cm-1. HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C16H1279BrN2O2 343.0077; Found 343.0067.
(S)-Methyl-2-(1,3-dioxoisoindolin-2-yl)-3-(4-hydroxy-3-(6-oxo-1-(pyridin-2-yl)-1,6-dihydropyridin-2-
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yl)phenyl)propanoate (4h): Yield 36% (17.8 mg), brown gummy oil, H NMR (400 MHz, DMSO-d6) δ 9.49 (s, 1H), 7.91
(m, 5H), 7.64 (t, J = 7.9 Hz, 1H), 7.46 – 7.30 (m, 1H), 7.28 (d, J = 7.9 Hz, 1H), 7.11 – 6.97 (m, 1H), 6.88 – 6.80 (m, 1H), 6.74
(d, J = 8.3 Hz, 1H), 6.43 (d, J = 9.1 Hz, 1H), 6.37 (d, J = 8.3 Hz, 1H), 5.10 (d, J = 4.9 Hz, 1H), 3.67 (s, 3H), 3.27 (m, 2H), 3.11
(m, 1H). 13C NMR (100 MHz, DMSO-d6) δ 169, 166.9, 162.1, 152.4, 151.5, 147.8, 146.8, 140.3, 136.9, 135.1, 131, 130.7,
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130.6, 126.2, 124.2, 123.6, 123.1, 121.9, 118.8, 115.1, 107, 52.7, 52.6, 32.7. FT-IR:
= 3422, 2952, 2855, 2926, 1774, 1744,
1716, 1654, 1617, 1543, 1508, 1467, 1432, 1388, 1244 cm-1. HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C28H22N3O6
496.1503; Found 496.1530.
6-((8R,9S,13S,14S)-3-Hydroxy-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H
cyclopenta[a]phenanthren-2-yl)-1-(pyridin-2-yl)pyridin-2(1H)-one (4i): Yield 42% (18.5 mg), pale brown gummy oil,
1H NMR (600 MHz, DMSO-d6) δ 9.31 (s, 1H), 8.31 (d, J = 9.2 Hz, 1H), 7.77 (t, J = 7.7 Hz, 1H), 7.53 (dd, J = 9.2, 6.8 Hz, 1H),
7.42- 7.32 (m, 1H), 7.25- 7.23 (m, 1H), 6.81 (s, 1H), 6.45 (d, J = 9.2 Hz, 1H), 6.33 (s, 1H), 6.17 (d, J = 6.8 Hz, 1H), 2.63 (dd,
J = 7.5, 3.2 Hz, 2H), 2.41 (dd, J = 19.2, 8.7 Hz, 1H), 2.15 (m, 1H), 2.10 – 1.95 (m, 2H), 1.95 – 1.87 (m, 1H), 1.87 – 1.78 (m,
1H), 1.72 (d, J = 12.6 Hz, 1H), 1.51 (m, 1H), 1.41 (m, 1H), 1.37 – 1.27 (m, 2H), 1.22 (d, J = 15.8 Hz, 2H), 0.78 (s, 3H). 13C
NMR (100 MHz, DMSO-d6) δ 219.5, 162.4, 152, 151.7, 148.2, 145.4, 140.4, 138.1, 137.3, 129.5, 127.6, 123.3, 119.5, 118.4,
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114.9, 107.6, 49.4, 47.2, 42.9, 37.7, 35.3, 31.2, 28.5, 25.8, 25.4, 21.1, 13.4. FT-IR: = 3433, 3238, 2926, 2859, 1735, 1654,
1544, 1436 cm-1. HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C28H29N2O3 441.2173; Found 441.2182.
3-(2-Hydroxy-4-methylphenyl)-2-(pyridin-2-yl)isoquinolin-1(2H)-one (4j): Yield 49% (16.1 mg), brown gummy oil, 1H
NMR (600 MHz, DMSO-d6) δ 9.43 (s, 1H), 8.30 (dd, J = 5.0, 1.8 Hz, 1H), 8.23 (d, J = 7.8 Hz, 1H), 7.80 – 7.76 (m, 2H), 7.72
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