Table 3. Copper-Catalyzed Indolation of THIQ.
entry | R | X | amt of THIQ (equiv) | yield (%) |
---|---|---|---|---|
1 (5h) | H | CH | 8.0 | 84 |
2 (5h) | H | CH | 4.0 | 85 |
3 (5h) | H | CH | 2.0 | 74 |
4 (5h) | H | CH | 0.8 | 48 |
5 (5h) | H | CH | 0.4 | 53 |
6 (5i) | 1-Me | CH | 0.8 | 1 |
7 (5j) | 2-Me | CH | 0.8 | 43 |
8 | 3-Me | CH | 0.8 | ncb |
9 (5l) | 5-OMe | CH | 0.8 | 48 |
10 (5l) | 5-OMe | CH | 2.0 | 71 |
11 (5m) | 5-NO2 | CH | 0.8 | 53a |
12 (5m) | 5-NO2 | CH | 2.0 | 62a |
13 (5n) | 5-COOMe | CH | 2.0 | 58 |
14 (5p) | 6-Cl | CH | 0.8 | 46 |
15 (5q) | 7-NO2 | CH | 0.8 | 2 |
16 (5r) | N | 0.8 | 43 | |
17 (5t) | 7-Me | CH | 0.8 | 48 |
18 (5t) | 7-Me | CH | 2.0 | 68 |
Reaction time: 2 days.
nc = no conversion.