6 of 8
CHAI ET AL.
127.8, 127.6, 126.4, 125.2, 123.2, 120.3, 106.7, 105.3,
27.3, 22.8.
1 H), 6.04 (t, J = 3.0 Hz, 1 H), 1.39 (s, 9 H). 13C{1H} NMR
(CDCl3, 100 MHz): δ 143.4, 133.2, 130.5, 128.9, 125.8,
123.6, 105.8, 104.6, 31.6, 30.7.
4.7 | 2‐Isopropyl‐4,5‐dihydro‐1H‐benzo[g]
indole (3e)
4.12 | 2,5‐diphenyl‐1H‐pyrrole (3j)
127 mg, 60% yield, colorless oil. 1H NMR (CDCl3,
400 MHz): δ 7.92 (s, br, 1 H), 7.05–6.96 (m, 3 H), 6.88
(t, J = 7.3 Hz, 1 H), 5.73 (d, J = 1.4 Hz, 1 H), 2.84–2.78
(m, 3 H), 2.59 (t, J = 7.6 Hz, 2 H), 1.18 (d, J = 6.9 Hz,
3:3 H). 13C{1H} NMR (CDCl3, 100 MHz): δ 140.1, 134.4,
129.6, 128.3, 126.4, 126.2, 124.4, 120.3, 117.8, 103.3, 30.1,
27.4, 22.8, 22.0.
140 mg, 64% yield, colorless solid, 1H NMR (CDCl3,
400 MHz): δ 8.56 (s, br, 1 H), 7.53 (d, J = 7.7 Hz, 4 H),
7.39 (t, J = 7.7 Hz, 4 H), 7.23 (t, J = 7.0 Hz, 2 H), 6.59
(d, J = 2.3 Hz, 2 H). 13C{1H} NMR (CDCl3, 100 MHz): δ
133.2, 132.6, 129.0, 126.5, 123.9, 108.0.
4.13 | 2‐Benzyl‐5‐phenyl‐1H‐pyrrole (3 k)
170 mg, 73% yield, colorless solid, 1H NMR (CDCl3,
400 MHz): δ 8.13 (s, br, 1 H), 7.51–7.36 (m, 9 H), 7.30–
7.26 (m, 1 H), 6.59 (t, J = 3.0 Hz, 1 H), 6.19–6.18 (m, 1
H), 4.13 (s, 2 H). 13C{1H} NMR (CDCl3, 100 MHz): δ
139.4, 132.9, 132.1, 131.6, 128.9, 128.8, 128.7, 126.6,
125.9, 123.5, 108.7, 106.2, 34.3.
4.8 | 2‐(5‐isopropyl‐1H‐pyrrol‐2‐yl)
pyridine (3f)
102 mg, 55% yield, yellow oil, 1H NMR (CDCl3,
400 MHz): δ 9.48 (s, br, 1 H), 8.43–8.42 (m, 1 H), 7.60–
7.56 (m, 1 H), 7.51–7.49 (m, 1 H), 7.00–6.96 (m, 1 H),
6.64–6.62 (m, 1 H), 6.01 (t, J = 3.2 Hz, 1 H), 3.03–2.93
(m, 1 H), 1.31 (d, J = 6.9 Hz, 6 H). 13C{1H} NMR (CDCl3,
100 MHz): δ 150.9, 148.7, 141.8, 136.5, 129.9, 120.0, 117.9,
107.6, 105.5, 27.4, 22.7.
4.14 | 5‐(Naphthalen‐2‐yl)‐2,3‐diphenyl‐
1H‐pyrrole (3 l)
214 mg, 62% yield, colorless solid. 1H NMR (CDCl3,
400 MHz): δ 8.54 (s, br, 1 H), 7.90–7.80 (m, 4 H), 7.71
(dd, J = 8.5, 1.6 Hz, 1 H), 7.51–7.43 (m, 6 H), 7.36–7.21
(m, 6 H), 6.82 (d, J = 2.8 Hz, 1 H). 13C{1H} NMR (CDCl3,
100 MHz): δ 136.4, 133.9, 133.1, 132.4, 129.9, 129.7, 128.9,
128.8, 128.6, 128.5, 127.9, 127.8, 127.7, 127.2, 126.7, 126.1,
125.7, 124.1, 123.1, 121.2, 109.4.
4.9 | 2‐Cyclopropyl‐5‐isopropyl‐1H‐pyrrole
(3 g)
122 mg, 82% yield, colorless oil, 1H NMR (CDCl3,
400 MHz): δ 7.86 (s, br, 1 H), 5.89 (t, J = 2.9 Hz, 1 H),
5.85 (t, J = 2.9 Hz, 1 H), 3.03–2.93 (m, 1 H), 1.91–1.85
(m, 1 H), 1.36 (d, J = 6.9 Hz, 6 H), 0.92–0.87 (m, 2 H),
0.74–0.70 (m, 2 H). 13C{1H} NMR (CDCl3, 100 MHz): δ
137.6, 132.8, 103.4, 102.6, 27.1, 22.7, 8.2, 6.4.
4.15 | 5‐Isopropyl‐3‐methyl‐2‐phenyl‐1H‐
pyrrole (3 m)
4.10 | 2‐Methyl‐5‐phenyl‐1H‐pyrrole (3 h)
159 mg, 80% yield, colorless oil, 1H NMR (CDCl3,
400 MHz): δ 7.91 (s, br, 1 H), 7.51–7.45 (m, 4 H), 7.32–
7.28 (m, 1 H), 5.97 (d, J = 2.7 Hz, 1 H), 3.08–2.97 (m, 1
H), 2.36 (s, 3 H), 1.39 (d, J = 6.9 Hz, 6 H). 13C{1H} NMR
(CDCl3, 100 MHz): δ 138.8, 134.1, 128.7, 126.6, 126.1,
125.6, 116.1, 107.4, 27.2, 22.8, 12.7.
134 mg, 85% yield, colorless solid, 1H NMR (CDCl3,
400 MHz): δ 8.08 (s, br, 1 H), 7.43–7.41 (m, 2 H), 7.35–
7.32 (m, 2 H), 7.19–7.15 (m, 1 H), 6.42 (t, J = 3.0 Hz, 1
H), 5.98–5.97 (m, 1 H), 2.32 (s, 3 H). 13C{1H} NMR
(CDCl3, 100 MHz): δ 133.0, 130.9, 129.2, 128.9, 125.7,
123.4, 108.0, 106.3, 13.2.
4.16 | 5‐(tert‐butyl)‐3‐methyl‐2‐phenyl‐1H‐
4.11 | 2‐(tert‐butyl)‐5‐phenyl‐1H‐pyrrole
pyrrole (3n)
(3i)
154 mg, 72% yield, colorless oil, 1H NMR (CDCl3,
400 MHz): δ 7.74 (s, br, 1 H), 7.32–7.26 (m, 4 H), 7.12–
7.08 (m, 1 H), 5.78 (d, J = 2.9 Hz, 1 H), 2.16 (s, 3 H),
1.23 (s, 9 H). 13C{1H} NMR (CDCl3, 100 MHz): δ 141.8,
141 mg, 71% yield, white solid, 1H NMR (CDCl3,
400 MHz): δ 8.17 (s, br, 1 H), 7.49–7.47 (m, 2 H), 7.40–
7.36 (m, 2 H), 7.20 (t, J = 7.3 Hz, 1 H), 6.44 (t, J = 3.1 Hz,