Compound 2a
N,N-(4-(2-tert-butyl)phenanthridinyl)(8-quinolinyl)amine
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InChIKey YZNBMLFEBACLBI-UHFFFAOYSA-N
Compound data: 1H NMR (CDCl3)
Compound data: 1H NMR (C6D6)
Compound data: 13C{1H} NMR (CDCl3)
Compound data: 13C{1H} NMR (C6D6)
Compound data: 1H-1H COSY
Compound data: HSQC
Compound data: HMBC
Compound data: Crystallographic data
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
A 500 mL Teflon-stoppered flask was charged with Pd2(dba)3 (0.26 g, 0.30 mmol), rac-BINAP (0.42 g, 0.70 mmol) and toluene (30 mL). After stirring for 5 min, 8-bromoquinoline (2.00 g, 10.1 mmol), 1c (2.50 g, 10.1 mmol), and an additional 20 mL of toluene were added, followed by sodium tert-butoxide (NaOtBu; 1.4 g, 15.1 mmol). The reaction mixture was stirred and subject to reflux in an oil bath at 150 °C for 72 h. After cooling the flask, the volatiles were removed and the residue was taken up in dichloromethane. The suspension was then filtered over a silica plug and the solvent was removed to leave a brown solid. Isolated yield = 3.80 g (> 99 %). 1H NMR (CDCl3, 300 MHz, 25 °C): δ 10.53 (s, 1H, N2-H), 9.29 (s, 1H, C1-H), 8.98 (dd, 1H, JHH = 4.2, 1.7 Hz, C18-H), 8.68 (d, 1H, JHH = 8.4 Hz, C3-H), 8.21- 8.04 (m, 4H, C6-H, C13-H, C20-H, C26-H), 7.90 – 7.84 (m, 2H, C11-H, C25-H), 7.71 (ddd, 1H, JHH = 8.0, 7.0 1.1 Hz, C4-H), 7.55 (t, 1H, C5-H), 7.47 (dd, 1H, JHH = 8.2, 4.2 Hz, C19-H), 7.32 (dd, 1H, JHH = 8.2, 1.2 Hz, C24-H), 1.55 ppm (s, 9H, tBu). 1H NMR (C6D6, 500 MHz, 25 °C): δ 11.58 (s, 1H, N2-H), 9.10 (s, 1H, C1-H), 8.73 (dd, 1H, JHH = 4.3, 1.6 Hz, C18-H), 8.40 (d, 1H, JHH = 8.3 Hz, C3-H), 8.32 (s, 1H, C13-H), 8.12-8.05 (m, 2H, C11-H, C26-H), 7.59 (dd, 1H, JHH = 8.2, 1.6 Hz, C20-H), 7.44 (d, 1H, JHH = 7.9 Hz, C6-H), 7.39 (m, 2H, C4-H, C25-H), 7.20 (t, 1H, JHH = 7.4 Hz, C5-H), 7.06 (d, 1H, JHH = 8.2 Hz, C24-H), 6.83 (dd, 1H, JHH = 8.2, 4.1 Hz, C19-H), 1.46 ppm (s, 9H, tBu). 13C{1H} NMR (CDCl3, 75 MHz, 25 °C): δ 150.6 (C1), 150.5 (C12), 148.1 (C18), 140.2 (C21, 22 or 23),), 139.5 (C10 or 23),139.2 (C10 or 23), 134.0 (C20), 133.1 (C7 or 8), 130.7 (C8 or 9), 129.2 (C4), 129.1 (C21, 22 or 23), 128.9 (C6), 128.3 (C25), 127.3 (C2 or 7), 127.3 (C5), 124.3 (C2 or 7), 122.3 (C3), 121.7 (C19), 117.5 (C24), 110.6 (C13), 109.2 (C11), 108.9 (C26), 35.7 (C14), 31.7 ppm (C15,16,17). 13C{1H} NMR (C6D6, 125 MHz, 25 °C): δ 150.5 (C1), 150.5 (C12), 148.0 (C18), 140.8 (C21, 22 or 23),), 140.2 (C10 or 23),140.0 (C10 or 23), 135.9 (C20), 134.6 (C7 or 8), 133.3 (C8 or 9), 130.5 (C4), 129.5 (C21, 22 or 23), 129.0 (C6), 127.5 (C25), 127.3 (C2 or 7), 127.1 (C5), 124.7 (C2 or 7), 122.4 (C3), 121.8 (C19), 117.6 (C24), 110.3 (C13), 109.3 (C11), 108.9 (C26), 35.6 (C14), 31.7 ppm (C15,16,17). UV-Vis (CH3CN): λ (ε) 306 (9 680), 388 nm (12 270 M-1 cm-1).