St-Cyr et al.
JOCArticle
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Table 3, Entry 6. Isolated yield: 47%. H NMR (500 MHz,
CDCl3): δ (ppm) 7.21-7.08 (m, 9H), 6.86 (d, J = 8.0 Hz, 2H),
6.63-6.55 (m, 2H), 4.87 (s, 2H), 3.80 (s, 3H), 3.64 (s, 3H), 2.36 (s,
3H), 2.23 (s, 3H). 13C NMR (125 MHz, CDCl3): δ (ppm) 166.2,
159.0, 139.0, 138.3, 137.6, 132.2, 132.0, 130.4, 129.6, 128.5,
128.0, 126.7, 125.9, 124.1, 118.7, 113.6, 112.5, 55.1, 50.4, 48.1,
21.3, 11.7. HRMS (ESIþ) for C28H28NO3þ: calcd 426.20637,
found 426.20627 (error m/z = 0.2 ppm).
HRMS (ESIþ) for C24H27NO2Naþ: calcd 384.19340, found
384.19341 (error m/z = 0.1 ppm).
Table 4, Entries 8 and 9. Isolated yields: 83 and 61%,
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respectively. H NMR (400 MHz, CDCl3): δ (ppm) 7.32-7.20
(m, 3H), 7.18-7.07 (m, 4H), 6.86 (d, J = 7.2 Hz, 2H), 4.97 (s,
2H), 3.86 (s, 3H), 3.62 (s, 3H), 3.02-2.90 (m, 1H), 2.32 (s, 3H),
1.20 (d, J = 7.2 Hz, 6H). 13C NMR (75 MHz, CDCl3): δ (ppm)
167.6, 165.3, 140.6, 138.7, 137.7, 136.9, 130.6, 129.1, 129.0,
128.1, 127.7, 125.7, 113.8, 113.4, 52.1, 51.6, 48.0, 26.7, 21.59,
21.55. HRMS (ESIþ) for C25H28NO4þ: calcd 406.20129, found
406.20093 (error m/z = 0.9 ppm).
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Table 4, Entry 1. Isolated yield: 84%. H NMR (400 MHz,
CDCl3): δ (ppm) 7.37 (d, J = 8.8 Hz, 2H), 7.33 (d, J = 8.8 Hz,
2H), 7.00-6.90 (m, 4H), 6.68 (s, 1H), 5.66-5.54 (m, 1H), 5.02 (d,
J = 10.4 Hz, 1H), 4,66 (d, J = 17,2 Hz, 1H), 4.42-4.32 (m, 2H),
4.13 (q, J = 7.2, 2H), 3.846 (s, 3H), 3.838 (s, 3H), 1.16 (t, J = 6.8,
3H). 13C NMR (75.5 MHz, CDCl3): δ (ppm) 165.1, 159.8, 159.5,
139.3, 134.7, 134.5, 132.2, 130.9, 125.5, 124.7, 116.6, 114.0,
113.8, 113.5, 110.2, 59.5, 55.5, 55.4, 47.2, 14.5. HRMS (ESIþ)
for C24H26NO4þ: calcd 392.18564, found 392.18520 (error
m/z = 1.1 ppm).
Table 4, Entry 10. Isolated yield: 44%. 1H NMR (400 MHz,
CDCl3): δ (ppm) 7.42-7.33 (m, 3H), 7.32-7.23 (m, 6H),
6.98-6.92 (m, 2H), 4.93 (m, 2H), 3.81 (m, 3H), 3.67 (m, 3H).
13C NMR (125 MHz, CDCl3): δ (ppm) 165.5, 164.1, 137.3,
136.3, 130.4, 130.0, 128.8, 128.3, 128.0, 127.0, 126.9, 115.5,
115.0, 51.7, 51.5, 51.2. HRMS (ESIþ) for C21H20NO4þ: calcd
350.13869, found 350.13827 (error m/z = 1.2 ppm).
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Table 4, Entry 11. Isolated yield: 30%. 1H NMR (300 MHz,
CDCl3): δ (ppm) 8.55 (d, J = 7.9 Hz, 1H), 7.59-7.49 (m, 3H),
7.48-7.42 (m, 1H), 7.42-7.35 (m, 2H), 7.07-7.00 (m, 2H), 6.79 (d,
J = 7.4 Hz, 1H), 4.02 (s, 3H), 3.88 (s, 3H), 3.72 (s, 3H). 13C NMR
(75.5 MHz, CDCl3): δ (ppm) 168.0, 165.3, 160.5, 132.5, 129.8,
128.5, 128.4, 128.2, 127.8, 127.4, 125.5, 124.5, 121.9, 121.5, 117.1,
114.4, 114.2, 109.2, 52.6, 52.8, 52.0. HRMS for C23H20NO5þ: calcd
390.13360, found 390.13434 (error m/z = 1.9 ppm).
Table 4, Entry 2. Isolated yield: 89%. H NMR (500 MHz,
CDCl3): δ (ppm) 7.38-7.26 (m, 4H), 7.21 (d, J = 7.0 Hz, 2H),
6.95 (d, J = 8.0 Hz, 2H), 6.69 (s, 1H), 5.65-5.55 (m, 1H), 5.01
(d, J = 10.0, 1H), 4.65 (d, J = 17.5 Hz, 1H), 4.39 (s, 2H), 3.85 (s,
3H), 3.68 (s, 3H), 2.39 (s, 3H). 13C NMR (125.7 MHz, CDCl3): δ
(ppm) 165.5, 159.9, 139.8, 137.8, 134.8, 134.7, 132.2, 130.1,
129.45, 129.36, 124.4, 116.7, 113.6, 113.4, 110.3, 55.4, 51.0,
47.2, 21.5. HRMS (ESIþ) for C23H24NO3þ: calcd 362.17507,
found 362.17471 (error m/z = 1.0 ppm).
Table 4, Entry 12. Isolated yield: 60%. 1H NMR (400 MHz,
CDCl3): δ (ppm) 7.54 (d, J = 7.6 Hz, 2H), 7.40-7.10 (m, 11H),
7.05-6.95 (m, 2H), 6.93-6.80 (m, 4H), 5.26 (s, 2H). 13C NMR
(75.5 MHz, CDCl3): δ (ppm) 192.0, 139.2, 137.8, 136.1, 132.3,
131.4, 130.1, 130.0, 129.2, 128.9, 128.5, 128.1, 127.7, 127.1,
126.1, 49.1. HRMS (ESIþ) for C32H20NO7þ: calcd 530.12343,
found 530.12378 (error m/z = 0.7 ppm).
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Table 4, Entry 3. Isolated yield: 90%. H NMR (400 MHz,
CDCl3):δ(ppm) 7.38(d, J= 8.4 Hz, 2H), 7.30 (d, J= 8.0 Hz, 2H),
7.24 (d, J = 7.6 Hz, 2H), 6.95 (d, J = 8.4 Hz, 2H), 6.69 (s, 1H),
5.68-5.55 (m, 1H), 5.03 (d, J = 10.4 Hz, 1H), 4.67 (d, J = 17.2 Hz,
1H), 4.39 (s, 2H), 3.85 (s, 3H), 3.69 (s, 3H), 2.42 (s, 3H). 13C NMR
(100.6 MHz, CDCl3): δ (ppm) 165.2, 159.3, 139.6, 138.2, 134.44,
134.38, 130.7, 130.5, 129.1, 128.7, 125.1, 116.4, 113.8, 113.0, 109.9,
55.3, 50.8, 46.9, 21.5. HRMS (ESIþ) for C23H24NO3þ: calcd
362.17507, found 362.17487 (error m/z = 0.6 ppm).
Table 4, Entry 13. Isolated yield: 32%. 1H NMR (300 MHz,
CDCl3): δ (ppm) 7.48 (s, 1H), 7.44-7.35 (m, 2H), 7.18-7.07 (m,
2H), 6.51-6.46 (m, 2H), 6.44-6.40 (m, 1H), 6.19 (d, J = 3.3 Hz,
1H), 4.14 (q, J = 7.2 Hz, 2H), 1.162 (t, J = 7.2 Hz, 3H). 13C NMR
(125 MHz, CDCl3): δ (ppm) 162.2 (d, 1JC-F = 246.9 Hz), 147.9,
141.4, 134.9, 131.0 (d, 2JC-F = 7.9 Hz), 129.6 (d, 4JC-F = 3.4 Hz),
125.0, 115.3 (d, 3JC-F = 21.5 Hz), 111.1, 109.4, 109.3, 106.3, 40.2,
16.4. HRMS (ESIþ) for C16H15NOFþ: calcd 256.11322, found
256.11293 (error m/z = 1.1 ppm).
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Table 4, Entry 4. Isolated yield: 74%. H NMR (300 MHz,
CDCl3): δ (ppm) 7.53 (s, 1H), 7.42-7.31 (m, 2H), 7.16-7.04 (m,
2H), 6.87 (d, J = 3.4 Hz, 1H), 6.54-6.50 (m, 1H), 6.48 (s, 1H),
5.92-5.76 (m, 1H), 5.14 (d, J = 10.6 Hz, 1H), 4,79 (d, J = 17.3
Hz, 1H), 4.72-4.63 (m, 2H). 13C NMR (75.5 MHz, CDCl3): δ
(ppm) 164.7, 161.4, 143.8, 143.0, 136.0, 133.8, 131.6, 131.5,
127.30, 127.26, 117.1, 117.0, 116.1, 115.8, 112.5, 111.9, 111.1,
92.4, 48.8. HRMS (ESIþ) for C18H14FN2Oþ: calcd 293.10846,
found 293.1091 (error m/z = 2.0 ppm).
Table 4, Entry 14. Isolated yield: 42%. 1H NMR (500 MHz,
CDCl3): δ (ppm) 7.22-7.07 (m, 5H), 7.04-6.93 (m, 6H), 6.77 (d,
J = 9.0 Hz, 2H), 6.47 (s, 1H), 6.45 (s, 1H), 3.79 (s, 3H), 2.30 (s,
3H). 13C NMR (125 MHz, CDCl3): δ (ppm) 158.4, 136.0, 135.8,
135.6, 133.7, 132.0, 130.4, 129.8, 128.62, 128.56, 127.8, 126.0,
113.9, 109.5, 109.3, 55.3, 21.0. HRMS (ESIþ) for C24H22NOþ:
calcd 340.16959, found 340.16952 (error m/z = 0.2 ppm). Note:
rapid H-D exchange in CDCl3 yielded extra carbon and MS
signals. 13C NMR (125 MHz, CDCl3): δ (ppm) 135.9, 135.5,
109.4, 109.2. HRMS (ESIþ) for C24H21DNOþ: calcd 341.17587,
found 341.17587 (error m/z = 0.0 ppm).
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Table 4, Entry 5. Isolated yield: 69%. H NMR (500 MHz,
CDCl3): δ (ppm) 7.42-7.34 (m, 3H), 7.30 (d, J = 7.5 Hz, 2H),
7.15-7.09 (m, 2H), 6.58 (s, 1H), 4.05 (q, J = 7.5 Hz, 2H), 2.42 (s,
3H), 1.03 (t, J = 7.4 Hz). 13C NMR (125 MHz, CDCl3): δ (ppm)
142.5, 139.3, 132.4, 129.6, 129.5, 127.5, 127.4, 127.3, 126.7, 126.5,
117.0, 113.3, 92.8, 40.4, 21.3, 16.2. HRMS (ESIþ) forC18H17N2Sþ:
calcd 293.11070, found 293.11030 (error m/z = 1.3 ppm).
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Table 4, Entry 6. Isolated yield: 67%. H NMR (400 MHz,
CDCl3): δ (ppm) 7.35-7.22 (m, 8H), 6.93 (d, J = 7.2 Hz, 2H),
6.72 (s, 1H), 5.19 (s, 2H), 3.83 (s, 3H), 3.25-3.13 (m, 1H), 1.29
(d, J = 7.2 Hz, 6H). 13C NMR (100 MHz, CDCl3): δ (ppm)
165.3, 146.2, 138.4, 133.6, 132.7, 129.3, 128.8, 128.4, 127.6,
127.3, 125.5, 111.6, 111.4, 50.9, 48.3, 26.7, 20.1. HRMS (ESIþ)
for C22H24NO2þ: calcd 334.18016, found 334.17984 (error
m/z = 1.0 ppm). Anal. Calcd for C22H23NO2: C, 79.25; H,
6.95; N, 4.20. Found: C, 79.12; H, 7.18; N, 4.07.
Table 4, Entry 15. Isolated yield: 35%. 1H NMR (500 MHz,
CDCl3): δ (ppm) 7.99 (s, 1H), 7.97-7.91 (m, 3H), 7.68 (d, J = 8.0
Hz, 1H), 7.64-7.46 (m, 6H), 7.43-7.36 (m, 1H), 6.45 (s, 1H), 6.39
(s, 1H), 4.25 (q, 2H, J = 7.0 Hz), 0.91 (t, 3H, J = 7.0 Hz). 13
C
NMR (125 MHz, CDCl3): δ (ppm) 136.3, 135.9, 134.0, 133.4,
132.3, 131.5, 129.0, 128.4, 127.95, 127.94, 127.7, 127.4, 127.3, 127.0,
126.3, 125.8, 110.1, 109.7, 40.1, 16.1. HRMS (ESIþ) for C22H20Nþ:
calcd 298.15903, found 298.15869 (error m/z = 1.1 ppm). Note:
rapid H-D exchange in CDCl3 yielded extra carbon and MS
signals. 13C NMR (125 MHz, CDCl3): δ (ppm) 136.2, 135.8, 110.0,
109.6. HRMS (ESIþ) for C22H19DNþ: calcd 299.16530, found
299.16490 (error m/z = 1.3 ppm).
Table 4, Entry 7. Isolated yield: 24%. 1H NMR (500 MHz,
CDCl3): δ (ppm) 7.36 (d, J = 8.0 Hz, 2H), 7.32-7.00 (m, 6H),
6.30 (s, 1H), 4.92 (s, 2H), 3.97 (q, J = 7.5 Hz, 2H), 2.42 (s, 3H),
2.41 (s, 3H), 2.34 (q, J = 7.5 Hz, 2H), 1.14 (t, J = 7.5 Hz, 3H),
0.87 (t, 3H, J = 7.0 Hz). 13C NMR (125 MHz, CDCl3): δ (ppm)
174.7, 137.6, 136.8, 134.4, 130.76, 130.74, 130.5, 129.1, 129.0,
116.3, 116.2, 109.8, 60.08, 60.06, 39.7, 27.7, 21.24, 21.17, 16.2, 9.1.
Table 4, Entry 16. Isolated yield: 63%. 1H NMR (300 MHz,
CDCl3): δ (ppm) 7.23-7.13 (m, 3H), 6.89 (d, J = 8.4 Hz, 2H),
6.66 (d, J = 6.9 Hz, 2H), 6.52 (d, J = 8.7 Hz, 2H), 5.21 (s, 2H),
4272 J. Org. Chem. Vol. 75, No. 12, 2010