Beilstein Journal of Organic Chemistry 2009, 5, No. 35.
MHz, CDCl3): δ 8.88 (dd, J = 4.1, 1.5 Hz, 1H), 8.25 (d, J = 8.1 4.28; H, 4.31; found C, 80.77; N, 4.56; H, 4.09. HRMS calcd.
Hz, 1H), 8.01 (d, J = 8.1 Hz, 1H), 7.66–7.73 (m, 3H), 7.40–7.47 for C22H14FNO: 327.1059; found 327.1046.
(m, 4H), 7.20–7.33 (m, 5H). 13C NMR (100 MHz, CDCl3): δ
198.8, 151.1, 146.6, 140.5, 139.3, 137.9, 137.4, 135.7, 133.0,
129.6, 129.3, 128.7, 128.6, 128.3, 128.2, 127.7, 127.0, 121.4.
HRMS calcd. for C22H15NO: 309.1154; found 309.1145.
Phenyl-[6-(trimethylsilyl)quinolin-8-yl]methanone (4h).
Following the general MACOS benzannulation protocol, 2-(2-
phenylethynyl)-nicotinaldehyde (1f) and TMS acetylene were
reacted and 800 μL of the crude reaction mixture were
collected. Purification by flash chromatography (20% ethyl
Phenyl-(6-phenylquinolin-8-yl)-methanone (4f). 1H NMR acetate in pentane) afforded 70.0 mg of 4h as a pale-brown oil
(400 MHz, CDCl3): δ 8.86 (dd, J = 4.1, 1.5 Hz, 1H), 8.29 (dd, J (58% yield). 1H NMR (400 MHz, CDCl3): δ 8.82 (dd, J = 4.1,
= 8.1, 1.5 Hz, 1H), 8.16 (d, J = 2.0 Hz, 1H), 8.03 (d, J = 2.0 Hz, 1.5 Hz, 1H), 8.21 (dd, J = 8.1, 1.5 Hz, 1H), 8.11 (d, J = 1.6 Hz,
1H), 7.92 (dd, J = 8.1, 1.5 Hz, 2H), 7.75 (dd, J = 8.1, 1.5 Hz, 1H), 7.84–7.87 (m, 3H), 7.55 (t, J = 7.6 Hz, 1H), 7.38–7.44 (m,
2H), 7.59 (t, J = 7.1 Hz, 1H), 7.49–7.56 (m, 2H), 7.40–7.49 (m, 3H), 0.38 (s, 9H). 13C NMR (100 MHz, CDCl3): δ 198.5,
4H). 13C NMR (100 MHz, CDCl3): δ 197.7, 150.8, 145.6, 151.0, 146.4, 138.9, 138.3, 137.9, 136.0, 135.5, 133.2, 132.1,
139.8, 139.5, 138.7, 137.7, 136.2, 133.3, 130.3, 129.1, 128.5, 130.2, 128.3, 127.5, 121.7, 0.87. Anal. Calcd. for C19H19NOSi:
128.3, 128.1, 127.9, 127.5, 127.1, 122.0. Anal. Calcd. for C, 74.71; N, 4.59; H, 6.27; found C, 74.93; N, 4.62; H, 6.07.
C22H15NO: C, 85.40; N, 4.53; H, 4.89; found C, 84.98; N, 4.32; HRMS calcd. for C19H19NOSi: 305.1236; found 305.1232.
H, 4.62. HRMS calcd. for C22H15NO: 309.1154; found
309.1143.
[6-(4-Bromophenyl)quinolin-8-yl]-phenylmethanone (4i).
Following the general MACOS benzannulation protocol, 2-(2-
phenylethynyl)-nicotinaldehyde (1f) and 1-bromo-4-ethynyl-
[6-(3-Fluorophenyl)quinolin-8-yl](phenyl)methanone (4g). benzene were reacted and 700 μL of the crude reaction mixture
Following the general MACOS benzannulation protocol, 2-(2- were collected. Purification by flash chromatography (20%
phenylethynyl)-nicotinaldehyde (1f) and 1-ethynyl-3-fluoroben- ethyl acetate in pentane) afforded 70.0 mg of 4i as a colourless
zene were reacted and 750 μL of the crude reaction mixture oil (52% yield). 1H NMR (400 MHz, CD2Cl2): δ 8.83 (dd, J =
were collected. Purification by flash chromatography (25% 4.1, 1.5 Hz, 1H), 8.35 (dd, J = 8.1, 1.5 Hz, 1H), 8.21 (d, J = 2.0
ethyl acetate in pentane) afforded 63.8 mg of 4g as a colourless Hz, 1H), 8.00 (d, J = 2.0 Hz, 1H), 7.85 (dd, J = 8.1, 1.5 Hz,
oil (54% yield). 1H NMR (400 MHz, CDCl3): δ 8.87 (dd, J = 2H), 7.60–7.76 (m, 4H), 7.44–7.56 (m, 3H), 7.34 (q, J = 9.0 Hz,
4.0, 1.5 Hz, 1H), 8.29 (dd, J = 8.1, 1.5 Hz, 1H), 8.15 (d, J = 2.0 1H). 13C NMR (150 MHz, CD2Cl2): δ 197.3, 150.7, 145.4,
Hz, 1H), 7.99 (d, J = 2.0 Hz, 1H), 7.90 (dd, J = 8.1, 1.5 Hz, 140.0, 138.5, 137.8, 137.5, 136.2, 133.2, 132.1, 129.8, 128.9,
2H), 7.60 (t, J = 7.1 Hz, 1H), 7.40–7.56 (m, 6H), 7.10–7.17 (m, 128.4, 128.3, 127.2, 126.9, 122.3, 122.1. HRMS calcd. for
1H). 13C NMR (100 MHz, CDCl3): δ 197.6, 163.3 (1J13C-19F = C22H14BrNO [M+H]+: 388.0337; found 388.0337.
245.0 Hz), 151.1, 145.7, 141.8, 141.7, 140.1, 137.6, 137.5,
136.2, 133.4, 130.6 (3J13C-19F = 8.5 Hz), 130.2, 128.4, 127.5,
127.3, 123.1, 122.1, 114.9 (2J13C-19F = 22.0 Hz), 114.4 (2J13C-
19F = 23.0 Hz). Anal. Calcd. for C22H14FNO: C, 80.72; N,
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